Sodium Bromide → cis-2-(2'-Pentylcyclopropyl)acetic acid

HRID 1490004

반응식

HRID 1490004 반응식
[CH:1](/O)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Br-].[Na+].[C:13](=[O:16])(O)[O-:14].[Na+]>ClCCl.O.[O-]Cl.[Na+]>[CH2:5]([C@H:6]1[CH2:7][C@H:8]1[CH2:9][C:13]([OH:14])=[O:16])[CH2:4][CH2:3][CH2:2][CH3:1]

참가 물질

7

반응물 3

HCID 253881Sodium BromideHCID 516892Sodium BicarbonateHCID 88386594Cis-nonen-1-ol

생성물 1

HCID 22846771cis-2-(2'-Pentylcyclopropyl)acetic acid

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 23665760Sodium Hypochlorite용매

실험 절차

Cis-nonen-1-ol (10.0 g) is subjected to the cyclopropanation conditions as described in the preparation of Example 52. The resulting residue is taken up in 100 mL of dichloromethane at 0° C., followed by the addition of 800 mg of sodium bromide in 2 mL of water and 150 mg of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical. To this mixture is added 1.50 g of Aliquot 336 followed by the dropwise addition of 9.2 g of sodium bicarbonate in 230 mL of 5% NaOCl. The aqueous phase is made basic, separated from the organic phase and acidified with concentrated HCl, and then extracted three times with dichloromethane. The combined organic layers are washed with water, dried over MgSO4, and concentrated in vacuo to give cis-2-(2'-pentylcyclopropyl) acetic acid.

후처리

  1. customas described in the preparation of Example 52
  2. additionTo this mixture is added 1.50 g of Aliquot 336
  3. customseparated from the organic phase
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic layers are washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fbd4fcdd0c3e4f2bac86c60e0c45fa3b
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05679801

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