HCID 67148514, compound → HCID 67147988, compound

HRID 2428062Notes

Reaction equation

HRID 2428062 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C@@H:7]([CH3:50])[C@H:8]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)[CH2:9][C@@H:10]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[CH2:11][O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C>C(Cl)Cl.C1(C)C=CC=CC=1>[Si:13]([O:12][CH2:11][C@H:10]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)[CH2:9][C@@H:8]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1)[C@H:7]([CH3:50])[CH:6]=[CH:5][CH2:4][OH:3])([C:26]([CH3:29])([CH3:27])[CH3:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 67148514HCID 67148514, compound

Product 1

HCID 67147988HCID 67147988, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ester 91 (600 mg, 0.84 mmol) in CH2Cl2 (6 mL) at −40° C. under argon was added slowly over 10 min via syringe DibalH in toluene (9 mL, 1M). After 30 min at −40° C., the reaction mixture was quenched by slow addition of MeOH (0.6 mL) and warmed to rt. The reaction mixture was poured into a vigorously stirred solution of saturated Rochelle salt in H2O (8 mL) and EtOAc (12 mL) and stirred overnight. The aqueous layer was separated and extracted with EtOAc (3×5 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude mixture was purified by flash chromatography (20% EtOAc in hexanes) to produce 450 mg (80%) of the alcohol, a clear liquid: 1H NMR (300 MHz, CDCl3) δ 7.70-7.66 (m, 4H), 7.39-7.35 (m, 6H), 7.21-7.18 (m, 4H), 6.85-6.82 (m, 4H), 5.68-5.65 (m, 2H), 4.64 (d, J=11.1 Hz, 1H), 4.51 (d, J=11.0 Hz, 1H), 4.46 (d, J=11.1 Hz, 1H), 4.24 (d, J=11.0 Hz, 1H), 4.10-4.06 (m, 2H), 3.78 (s, 6H), 3.81-3.52 (m, 4H), 2.60-2.56 (m, 1H), 1.57-1.51 (m, 2H), 1.05 (s, 9H), 1.03 (d, J=6.8 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 159.0, 135.6, 135.1, 133.5 (2C), 131.1, 130.3, 130.0, 127.6, 129.4, 129.6, 83.1, 75.2, 72.4, 72.2, 64.4, 63.7, 55.2, 34.7, 26.8, 19.2, 15.4; IR (thin film) 3295, 3045, 2958, 2941, 2910, 2857, 1241, 1097 cm−1; HRMS (EI) cald for C41H52O6Si 668.3599, found 668.3596.

Workup

  1. customthe reaction mixture was quenched by slow addition of MeOH (0.6 mL)
  2. additionThe reaction mixture was poured into a vigorously stirred solution of saturated Rochelle salt in H2O (8 mL) and EtOAc (12 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc (3×5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude mixture was purified by flash chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-db187b576a9343dea24deea7916195cf
Source dataset
uspto-grants-2011_06
Patent number
US07968736B2

Reaction notes

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