tert-Butyl acrylate → tert-Butyl 3-[(1S)-2-benzyloxy-1-methylethoxy]propanoate

HRID 1926888Notes

Reaction equation

HRID 1926888 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([OH:12])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].[H-].[Na+].[Cl-].[NH4+]>>[C:18]([O:17][C:13](=[O:16])[CH2:14][CH2:15][O:12][C@@H:10]([CH3:11])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 4

HCID 15458tert-Butyl acrylateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13197475(2S)-1-(benzyloxy)propan-2-ol

Product 1

HCID 58016790tert-Butyl 3-[(1S)-2-benzyloxy-1-methylethoxy]propanoateYield 52%

Conditions

Temperature
0 °C

Procedure

Cool a mixture of 20 g (120.3 mmol) (+)-(S)-1-benzyloxy-2-propanol and 123 g (962 mmol) tert.-butyl acrylate to 0° C. and add 962 mg (24 mmol, 60%) sodium hydride in several portions. Stir the mixture for 10 min at 0° C., then carefully add satd. ammonium chloride solution. After phase separation, extract the aqueous phase twice with dichloromethane. Combine the organic phases, dry over magnesium sulphate and concentrate under vacuum, then at high vacuum. Purify the raw product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 30:1). 18.4 g of the target compound (51.9% of theor.) is obtained.

Workup

  1. temperatureCool
  2. additioncarefully add
  3. customAfter phase separation
  4. extractionextract the aqueous phase twice with dichloromethane
  5. dry with materialdry over magnesium sulphate
  6. concentrationconcentrate under vacuum
  7. customPurify the raw product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 30:1)

Sources & evidence

ORD record
ord-44e1620a36534cf78ced5e650134d456
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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