Dimethylformamide → HCID 15461531, compound

HRID 1289889Notes

Reaction equation

HRID 1289889 reaction equation
[OH:1][CH2:2][C:3]1([CH3:16])[O:8][C:7]2[C:9]([CH3:15])=[C:10]([CH3:14])[CH:11]=[C:12]([CH3:13])[C:6]=2[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].CN(C)C=[O:34]>O>[Si:23]([O:1][CH2:2][C:3]1([CH3:16])[O:8][C:7]2[C:9]([CH3:15])=[C:10]([CH3:14])[C:11]([OH:34])=[C:12]([CH3:13])[C:6]=2[CH2:5][CH2:4]1)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 19601130HCID 19601130, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15461531HCID 15461531, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-hydroxy,-2-hydroxymethyl-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran, (3.14 g, 46.1 mmol), prepared by the reduction of the commercially available acid (Aldrich) using lithium aluminum hydride, and t-butyldimethylsilyl chloride (3.06 g, 20.3 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 23 hours. The reaction mixture was diluted with water (200 mL) and the product extracted with ethyl acetate (4×50 mL). The combined organic extracts were dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with a gradient elution of hexane/ethyl acetate to give 5.38 g (83.8% yield) of 2-(t-butyldimethylsilyloxymethyl)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran as an oil.

Workup

  1. extractionthe product extracted with ethyl acetate (4×50 mL)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel with a gradient elution of hexane/ethyl acetate

Sources & evidence

ORD record
ord-957a3446e5354eac9644cca3fdc185c6
Source dataset
uspto-grants-1998_05
Patent number
US05750564

Reaction notes

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