m-Chloroperbenzoic acid → Methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate

HRID 1581118노트

반응식

HRID 1581118 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=[CH:8][CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]2[O:34][CH:8]2[CH:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:3]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

생성물 1

HCID 21561498Methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (1.0 g.) [prepared as described in Example 5], metachlorperbenzoic acid (2.0 g.) and dichloromethane (30 ml.) was refluxed for days. The precipitated metachlorbenzoic acid was filtered from the cooled solution and washed with dichloromethane. The filtrate was washed successively with sodium sulphite solution, twice with 5% sodium bicarbonate solution and finally water, dried over sodium sulphate and evaporated to give methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-epoxy-1-octyl)cyclopentyl]heptanoate (0.96 g.,92%), νmax 3450 cm-1, 1730 cm-1 and 1170 cm-1.

후처리

  1. filtrationThe precipitated metachlorbenzoic acid was filtered from the cooled solution
  2. washwashed with dichloromethane
  3. washThe filtrate was washed successively with sodium sulphite solution, twice with 5% sodium bicarbonate solution and finally water
  4. dry with materialdried over sodium sulphate
  5. customevaporated

출처 및 근거

ORD 기록
ord-79cec05e01ae488ead16616f98a82031
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03935261

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