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

HRID 367300
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 367300
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]
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Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f7ae5977dd42433b9bb036c7395e839c
Quelldatensatz
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06133279

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