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

HRID 367300
Notes
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Reaction equation

HRID 367300 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f7ae5977dd42433b9bb036c7395e839c
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133279

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes