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Dimethyl Sulfoxide → 4,6-Di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran

HRID 367300
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HRID 367300 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:15]1[C:20]2[CH2:21][C:22]([CH2:25][OH:26])([CH3:24])[O:23][C:19]=2[CH:18]=[C:17]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:16]=1[O:31][Si:32]([CH3:35])([CH3:34])[CH3:33])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.O>[C:11]([C:15]1[C:20]2[CH2:21][C:22]([CH:25]=[O:26])([CH3:24])[O:23][C:19]=2[CH:18]=[C:17]([C:27]([CH3:29])([CH3:28])[CH3:30])[C:16]=1[O:31][Si:32]([CH3:35])([CH3:34])[CH3:33])([CH3:12])([CH3:13])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 232880414,6-Di-t-butyl-2-hydroxymethyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran

생성물 1

HCID 232880364,6-Di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 0.43 ml of dimethyl sulfoxide in 12 ml of dichloromethane cooled to -78° C. under nitrogen was added dropwise 0.26 ml of oxalyl chloride. After 15 minutes, a solution of 4,6-di-t-butyl-2-hydroxymethyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran in 5 ml of dichloromethane was added dropwise. After further 15 minutes, 1.91 ml of triethylamine was added dropwise and then the mixture was slowly warmed to room temperature. After one hour, the reaction solution was poured into water and extracted with dichloromethane, and the combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was purified on a short column of silica gel eluting with n-hexane containing 9% ethyl acetate to give 1.04 g of 4,6-di-t-butyl-2-formyl-2-methyl-5-trimethylsilyloxy-2,3-dihydrobenzofuran containing impurities.

후처리

  1. waitAfter further 15 minutes
  2. waitAfter one hour
  3. extractionextracted with dichloromethane
  4. washthe combined organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified on a short column of silica gel eluting with n-hexane containing 9% ethyl acetate

출처 및 근거

ORD 기록
ord-f7ae5977dd42433b9bb036c7395e839c
출처 데이터셋
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06133279

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