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

HRID 976468

반응식

HRID 976468 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 (15 g, 7.97 mmol, 1.0 equiv.) in tetrahydrofuran (THF) (32.0 mL, 0.25M) at -20° C. was treated ##STR1## 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-b3ac6e9d9fa742418d9dcdfa0d60ee14
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05612380

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