8-Methoxy-8-oxooctanoic acid → Methyl 8-hydroxyoctanoate

HRID 47184

반응식

HRID 47184 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](O)=[O:11].B.C1COCC1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11]

참가 물질

5

반응물 2

HCID 5541918-Methoxy-8-oxooctanoic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 554055Methyl 8-hydroxyoctanoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of suberic acid monomethyl ester (1.5 g, 7.97 mmol, 1.0 equiv.) in tetrahydrofuran (THF) (32.0 mL, 0.25M) at −20° C. was treated dropwise with BH3.THF (1M solution in THF, 7.97 mL, 7.97 mmol, 1.0 equiv.). The reaction mixture was stirred overnight and was subsequently allowed to reach room temperature. The reaction mixture was then diluted with ethyl acetate (100 mL) and quenched with methanol (10 mL) and 10% HCl (10 mL). Extraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL), afforded methyl-8-hydroxy-octanoate (7) as a crude white solid.

후처리

  1. customto reach room temperature
  2. customquenched with methanol (10 mL) and 10% HCl (10 mL)
  3. extractionExtraction with NaHCO3 (1×20 mL), water (2×10 mL), and brine (1×10 mL)

출처 및 근거

ORD 기록
ord-01088546d2f44973907c42d83e6bd685
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699682B2

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