Methanol → Isobutyric acid 4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

HRID 16216Notes

Reaction equation

HRID 16216 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[C:7]([Si:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:12][CH2:13][CH:14]=[CH:15][CH2:16][OH:17])([CH3:10])([CH3:9])[CH3:8].C(N(C(C)C)CC)(C)C.CO>CN(C)C1C=CN=CC=1.ClCCl>[C:7]([Si:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:12][CH2:13][CH:14]=[CH:15][CH2:16][O:17][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 666569494-(tert-Butyl-diphenyl-silanyloxy)-but-2-en-1-ol

Product 1

HCID 66656955Isobutyric acid 4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (10.4 mL, 98.04 mmol) was added drop wise to a stirred and a cooled (0° C.) solution of the product of Example 5E (61.28 mmol), diisopropylethyl amine (21.3 mL, 122.56 mmol), and 4-dimethylaminopyridine (0.30 g, 3.0 mmol) in dry dichloromethane (150 mL). The resulting solution was allowed to stir at 0° C. for five hours. After the completion of reaction (monitored by TLC), methanol (5 mL) was added to quench excess acid chloride. The solvent was removed under reduced pressure and the resulting slurry was partitioned using diethyl ether (200 mL) and saturated NH4Cl (100 mL). The organic layer was washed successively with 20% NaHSO4, NaHCO3, brine, and it was dried over MgSO4. After removal of solvent, the crude oil was purified over silica gel column using 10% diethyl ether in hexanes to give the title compound as a colorless oil: (20.5 g, 84% over 2 steps).

Workup

  1. stirringto stir at 0° C. for five hours
  2. additionwas added
  3. customto quench excess acid chloride
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting slurry was partitioned
  6. washThe organic layer was washed successively with 20% NaHSO4, NaHCO3, brine, and it
  7. dry with materialwas dried over MgSO4
  8. customAfter removal of solvent
  9. customthe crude oil was purified over silica gel column

Sources & evidence

ORD record
ord-9ad6ee661c1b4e08a9c15f080823fbe0
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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