Potassium Hydroxide → HCID 66572241, compound

HRID 2252491Notes

Reaction equation

HRID 2252491 reaction equation
C[O:2][C:3](=[O:68])/[CH:4]=[CH:5]\[CH:6]=[CH:7]\[C@@H:8]([CH3:67])[C@@H:9]([O:59][Si:60]([C:63]([CH3:66])([CH3:65])[CH3:64])([CH3:62])[CH3:61])[CH2:10][C@H:11]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])/[CH:12]=[CH:13]\[C@H:14]([CH3:50])[C@H:15]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C@@H:16]([CH3:41])[CH2:17][C@@H:18]([CH3:40])[CH2:19][CH2:20][C@@H:21]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[C@H:22]([CH3:31])[C@@H:23]([OH:30])[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28].[OH-].[K+]>CCO.C1COCC1>[Si:60]([O:59][C@@H:9]([CH2:10][C@H:11]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:53])[CH3:54])/[CH:12]=[CH:13]\[C@H:14]([CH3:50])[C@H:15]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:44])[CH3:45])[C@@H:16]([CH3:41])[CH2:17][C@@H:18]([CH3:40])[CH2:19][CH2:20][C@@H:21]([O:32][Si:33]([C:36]([CH3:37])([CH3:38])[CH3:39])([CH3:35])[CH3:34])[C@H:22]([CH3:31])[C@@H:23]([OH:30])[C@@H:24]([CH3:29])/[CH:25]=[CH:26]\[CH:27]=[CH2:28])[C@H:8]([CH3:67])/[CH:7]=[CH:6]/[CH:5]=[CH:4]\[C:3]([OH:68])=[O:2])([C:63]([CH3:64])([CH3:65])[CH3:66])([CH3:62])[CH3:61]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11491612HCID 11491612, compound

Product 1

HCID 66572241HCID 66572241, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A stirred solution of alcohol 47 (25 mg, 24 μmol) in 3.4 mL of 12:5 EtOH/THF was treated with 1N aqueous KOH (0.24 mL) and the mixture was refluxed gently for 3 h. The ethanolic solution was concentrated and then diluted with Et2O (4 mL). After the solution was acidified to pH3 with 1N aqueous HCl, the organic phase was separated and aqueous phase was extracted with Et2O (2×5 mL). The combined organic phase was dried with MgSO4, filtered, concentrated and the residue was used without further purification: IR (CHCl3) 2956, 2929, 2857, 1693, 1635, 1600, 1471, 1462, 1254, 1088, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.33 (dd, J=15.2, 11.3 Hz, 1H), 6.61 (t, J=11.4 Hz, 1H), 6.61 (m, 1H), 6.07 (t, J=11.0 Hz, 1H), 6.02 (dd, J=15.8, 7.2 Hz, 1H), 5.58 (d, J=11.3 Hz, 1H), 5.39 (m, 2H), 5.23 (dd, J=11.0, 8.2 Hz, 1H), 5.18 (d, J=16.8 Hz, 1H), 5.09 (d, J=10.2 Hz, 1H), 4.50 (m, 1H), 3.92 (m, 1H), 3.73 (m, 1H), 3.46 (dd, J=7.3, 2.6 Hz, 1H), 3.34 (m, 1H), 2.78 (m, 1H), 2.54 (m, 2H), 1.66 (m, 4H), 1.42 (m, 4H), 1.24 (m, 3H), 1.01 (d, J=6.8 Hz, 3H), 0.95 (d, J=6.7 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H), 0.88 (m, 30H), 0.84 (m, 15H), 0.09 (s, 3H), 0.07 (s, 3H), 0.06 (s, 6H), 0.02 (s, 6H), 0.01 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 171.2, 148.2, 147.3, 135.2, 133.2, 132.7, 132.3, 123.0, 127.0, 117.7, 115.2, 79.9, 77.6, 76.5, 72.1, 66.4, 43.5, 42.6, 41.6, 37.8, 36.0, 35.8, 34.9, 32.1, 31.5, 30.6, 26.2, 25.93, 25.87, 20.3, 19.4, 18.4, 18.10, 18.05, 17.7, 15.3, 13.6, 6.9 −3.0, −3.4, −3.7, −4.1, −4.19, −4.24, −4.4; LRMS (ESI) 1029.7 [M+Na]+, 875.6, 743.6, 611.4, 593.4, 393.3; HRMS (ESI) calcd for C56H110O7Si4Na 1029.7226 [M+Na]+, found 1029.7274; [α]20D−25.7 (c 0.54, CHCl3).

Workup

  1. temperaturethe mixture was refluxed gently for 3 h
  2. concentrationThe ethanolic solution was concentrated
  3. additiondiluted with Et2O (4 mL)
  4. customthe organic phase was separated
  5. extractionaqueous phase was extracted with Et2O (2×5 mL)
  6. dry with materialThe combined organic phase was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was used without further purification

Sources & evidence

ORD record
ord-99d4118d551c45d09ef7190802af07bb
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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