Sulfuric Acid → methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoate

HRID 1382530

반응식

HRID 1382530 반응식
O=[Cr](=O)=O.C1C=CC=CN=1.C1C=CC=CN=1.[CH3:17][O:18][C:19](=[O:41])[CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][C@H:26]1[C@H:30]([Cl:31])[CH2:29][C@@H:28]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C@@H:27]1[CH2:39][OH:40].C(=O)(O)[O-].[Na+].S(=O)(=O)(O)O>ClCCl.C(OCC)C.O>[CH3:17][O:18][C:19](=[O:41])[CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25][C@H:26]1[C@H:30]([Cl:31])[CH2:29][C@@H:28]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[C@@H:27]1[CH:39]=[O:40]

참가 물질

8

반응물 4

HCID 1118Sulfuric AcidHCID 88565Trioxobis(pyridine)chromiumHCID 516892Sodium BicarbonateHCID 11428798(+/-)-(Z)-7-[(1R,2S,3R,5R)-5-chloro-2-hydroxymethyl-3-(tetrahydropyran-2-yloxy)-cyclopentyl]-5-heptenic acid methyl ester

생성물 1

HCID 11234130methyl (5Z)-7-[(1R,2R,3R,5R)-5-chloro-2-formyl-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]-5-heptenoate수율 86.5%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

9 g of Collins reagent is dissolved in 85 ml of dichloromethane, and a solution of 2 g of VI in 25 ml of dichloromethane is instilled with stirring in 5 minutes, stirred 15 minutes, diluted with 200 ml of diethyl ether, shaken with sodium bicarbonate solution, diluted sulfuric acid and salt water, dried over magnesium sulfate and concentrated by evaporation in a vacuum. 1.72 g of aldehyde VII is obtained as oil.

후처리

  1. stirringstirred 15 minutes
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

출처 및 근거

ORD 기록
ord-051427dba65341b6baa3b71a29f94bfe
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04806668

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