Water → Ethyl 3-[4-benzyloxyphenyl]-2-butoxypropanoate
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]=1Participants
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 the pet. ether (1:9) as an eluent to afford the title compound (0.7 g, 20%) as an oil.
Workup
- stirringstirring
- waitwas continued for 10 h at ca. 25° C
- extractionextracted with ethyl acetate 2×50 mL)
- washThe combined ethyl acetate layer was washed with water (50 mL), brine (25 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customthe solvent was evaporated
- customThe residue was chromatographed over silica gel using
- additiona mixture of ethyl acetate
Sources & evidence
- ORD record
- ord-ac255e3b1b65409b9bc7da613309fda8
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06608194B1
Reaction notes
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