Water → Ethyl 3-[4-benzyloxyphenyl]-2-butoxypropanoate

HRID 495702Notes

Reaction equation

HRID 495702 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:25](Br)[CH2:26][CH2:27][CH3:28].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:22][CH2:25][CH2:26][CH2:27][CH3:28])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

Product 1

HCID 21930967Ethyl 3-[4-benzyloxyphenyl]-2-butoxypropanoateYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of ethyl 3-[4-benzyloxyphenyl)-2-hydroxypropanoate (5.0 g, 16.6 mmol) (prepared in a similar manner as described in Ref: WO95/18125) in dry dimethyl formamide (5 mL) was added to a suspension of sodium hydride (0.1 g, 41.6 mmol) (60% dispersion in oil) in dry dimethyl formamide (3 mL) at 0° C. and stirring was continued for further 1 h. To the above reaction mixture n-butyl bromide (3.4 g, 24.0 mmol) was added at 0° C. and stirring was continued for 10 h at ca. 25° C. Water (30 mL) was added and extracted with ethyl acetate (2×50 mL). The combined ethyl acetate layer was washed with water (50 mL), brine (25 mL), dried (Na2SO4), filtered and the solvent was evaporated. The residue was chromatographed over silica gel using a mixture of ethyl acetate and and pet. ether (1:9) as an eluent to afford the title compound (0.7 g, 20%) as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for 10 h at ca. 25° C
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined ethyl acetate layer was washed with water (50 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was chromatographed over silica gel using
  9. additiona mixture of ethyl acetate and and pet. ether (1:9) as an eluent

Sources & evidence

ORD record
ord-59db7a523e444cc6b8d5ccd49a73e26b
Source dataset
uspto-grants-2005_09
Patent number
US06939988B1

Reaction notes

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