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

HRID 495702노트

반응식

HRID 495702 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 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.

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-59db7a523e444cc6b8d5ccd49a73e26b
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939988B1

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