Potassium Hydroxide → HCID 87737711, compound

HRID 2252494Notes

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+]>>[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

Reactant 2

HCID 14797Potassium Hydroxide

HCID 87736533HCID 87736533, compound

Product 1

HCID 87737711HCID 87737711, compound

Procedure

The procedure for 48 was used with 56 (56 mg, 55 μmol) and 1N aqueous KOH (0.54 mL) to yield 57, which was used without further purification: IR (CHCl3) 2956, 2929, 2857, 1693, 1634, 1471, 1462, 1254, 1082, 836, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.34 (dd, J=15.1, 11.4 Hz, 1H), 6.64 (ddd, J=16.5, 10.6, 10.5 Hz, 1H), 6.61 (t, J=11.2 Hz, 1H), 6.07 (t, J=11.0 Hz, 1H), 6.01 (dd, J=15.5, 7.2 Hz, 1H), 5.58 (d, J=11.3 Hz, 1H), 5.44-5.34 (m, 2H), 5.23 (dd, J=11.0, 8.2 Hz, 1H), 5.17 (d, J=18.0 Hz, 1H), 5.08 (d, J=10.1 Hz, 1H), 4.50 (m, 1H), 3.92 (m, 1H), 3.69 (m, 1H), 3.35 (m, 1H), 2.75 (m, 1H), 2.54 (m, 2H), 1.74-1.56 (m, 4H), 1.49-1.20 (m, 7H), 1.02 (d, J=6.8 Hz, 3H), 0.98 (d, J=7.2 Hz, 3H), 0.94 (d, J=7.0 Hz, 3H), 0.90-0.82 (m, 45H), 0.09-0.01 (m, 24H); 13C NMR (75 MHz, CDCl3) δ 171.1, 148.2, 147.4, 136.4, 132.7, 132.6, 129.6, 127.0, 117.4, 115.1, 79.8, 78.4, 74.2, 72.1, 66.5, 43.5, 42.6, 41.5, 36.0, 35.9, 35.8, 35.0, 31.9, 30.8, 29.7, 26.3, 26.0, 25.9, 20.4, 19.3, 18.5, 18.13, 18.08, 17.97, 17.4, 15.4, 13.7, 10.8, −3.0, −3.4, −3.7, −4.1, −4.2, −4.3, −4.4, −4.8; LRMS (ESI) 1029.8 [M+Na]+, 832.3, 758.3, 684.3, 610.2, 541.2; HRMS (ESI) calcd for C56H110O7Si4Na 1029.7226 [M+Na]+, found 1029.7255; [α]20D−6.5 (c 0.17, CHCl3).

Sources & evidence

ORD record: ord-4f60724908a145feae608bf945219abf
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07321046B2

Reaction notes

Loading…