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

HRID 1243814노트

반응식

HRID 1243814 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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 aided 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.

후처리

  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

출처 및 근거

ORD 기록
ord-92417c7372b945c4b9b0fa874c60363e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119198B2

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