Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl ester → Methyl 1-methyl-2-hydroxycyclopentanecarboxylate

HRID 275346노트

반응식

HRID 275346 반응식
[CH3:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C1COCC1>[CH3:1][C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:5][CH2:4][CH:3]1[OH:7]

참가 물질

4

반응물 2

HCID 121785Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl esterHCID 16684435Lithium tritertbutoxyaluminohydride

생성물 1

HCID 15577614Methyl 1-methyl-2-hydroxycyclopentanecarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To methyl 1-methyl-2-oxocyclopentanecarboxylate (20.0 g=128 mmol) in THF (800 ml) add portionwise lithium tri-t-butoxyaluminohydride (40.7 g=160 mmol). Stir 1 hr and partition between Et2O and 1.0N HCl. Dry and concentrate to obtain methyl 1-methyl-2-hydroxycyclopentanecarboxylate, largely the 1β-methyl-2β-hydroxy isomer, as an oil.

후처리

  1. custompartition between Et2O and 1.0N HCl
  2. customDry
  3. concentrationconcentrate

출처 및 근거

ORD 기록
ord-2e339b3ddf7b480091c4a4676c9a7df9
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393755

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