Dichloromethane → (1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl-ethyl tert-butyl(dimethyl)silyl ether

HRID 2056724Notes

Reaction equation

HRID 2056724 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[C@H:21]([CH2:22][CH2:23][OH:24])[O:20][CH2:19][CH2:18][C:17]=2[CH:25]=1.C(N(C(C)C)CC)(C)C.CN(C1C=CC=CN=1)C>CN(C)C=O>[Si:1]([O:24][CH2:23][CH2:22][C@H:21]1[C:16]2[CH:15]=[CH:14][C:13]([Br:12])=[CH:25][C:17]=2[CH2:18][CH2:19][O:20]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

Product 1

HCID 69307753(1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl-ethyl tert-butyl(dimethyl)silyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1M solution of tert-butyldimethylsilyl chloride in dichloromethane (30 mL, 30 mmol) was added dropwise under nitrogen to an ice/water-cooled solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (6.7 g, 24.4 mmol), diisopropylethylamine (6.7 g. 51.8 mmol) and dimethylaminopyridine (0.32 g, 2.5 mmol) in dry dimethylformamide (70 mL). After stirring overnight at room temperature, the mixture was quenched with ice/water and extracted with ether (2×). The combined organic extracts were washed with water (5×), dried (MgSO4) and evaporated in vacuo to give an oil. This was purified by flash chromatography on silica, eluting with ethyl acetate/hexane (0:100 to 10:90), to give the title compound as oil.

Workup

  1. customthe mixture was quenched with ice/water
  2. extractionextracted with ether (2×)
  3. washThe combined organic extracts were washed with water (5×)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto give an oil
  7. customThis was purified by flash chromatography on silica
  8. washeluting with ethyl acetate/hexane (0:100 to 10:90)

Sources & evidence

ORD record
ord-8bacdb707b1c4851a6b7b23db5318d1f
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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