rac-3,4-dihydro-2,5,7,8-tetramethyl-2-(2-propenyl)-6-(phenylmethoxy)-2H-1-benzopyran → (6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde

HRID 580375노트

반응식

HRID 580375 반응식
O=[O+][O-].[O:4]=O.[CH3:6][C:7]1([CH2:28][CH:29]=C)[CH2:12][CH2:11][C:10]2[C:13]([CH3:27])=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]([CH3:18])=[C:16]([CH3:17])[C:9]=2[O:8]1>CO>[CH3:6][C:7]1([CH2:28][CH:29]=[O:4])[CH2:12][CH2:11][C:10]2[C:13]([CH3:27])=[C:14]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]([CH3:18])=[C:16]([CH3:17])[C:9]=2[O:8]1

참가 물질

4

반응물 2

HCID 14210609rac-3,4-dihydro-2,5,7,8-tetramethyl-2-(2-propenyl)-6-(phenylmethoxy)-2H-1-benzopyranHCID 131711318Oxygen ozone

생성물 1

HCID 13422213(6-Benzyloxy-2,5,7,8-tetramethylchroman-2-yl)acetaldehyde

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
-78 °C

실험 절차

An ozone-oxygen gas mixture is passed into a solution of 0.67 g (2 mmoles) of rac-3,4-dihydro-2,5,7,8-tetramethyl-2-(2-propenyl)-6-(phenylmethoxy)-2H-1-benzopyran in 100 ml of methanol, with stirring, at -78° C. After the starting olefin has been consumed, the ozone flow is stopped and the solution is treated with excess dimethyl sulfide and allowed to warm to room temperature. The solution is concentrated in vacuo. The residue is chromatographed on silica gel giving rac-3,4-dihydro-2,5,7,8-tetramethyl-6-(phenylmethoxy)-2H-1-benzopyran-2-acetaldehyde, which can be converted to Vitamin E by the procedures in Helv. Chim. Acta set forth in Example 8.

후처리

  1. customAfter the starting olefin has been consumed
  2. additionthe solution is treated with excess dimethyl sulfide
  3. temperatureto warm to room temperature
  4. concentrationThe solution is concentrated in vacuo
  5. customThe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-95465a65c4164dbdb912a878af53938e
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752646

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