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

HRID 2056757Notes

Reaction equation

HRID 2056757 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:10]([CH2:11][CH2:12][OH:13])[O:9][CH2:8][CH2:7][C:6]=2[CH:14]=1.N1C=CN=C1.Cl[Si:21]([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)C>C1COCC1>[Si:21]([O:13][CH2:12][CH2:11][C@H:10]1[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:6]=2[CH2:7][CH2:8][O:9]1)([C:34]([CH3:37])([CH3:36])[CH3:35])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 94078tert-ButyldiphenylchlorosilaneHCID 536878432-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol

Product 1

HCID 693073122-((1S)-6-Bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethyl tert-butyl(diphenyl)silyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((1S)-6-bromo-3,4-dihydro-1H-2-benzopyran-1-yl)ethanol (3.0 g, 11.7 mmol) in dry THF (100 mL) was added imidazole (3.97 g, 58.4 mmol) and chloro-tert-butyl(diphenyl)silane (6.42 g, 23.4 mmol), and the mixture stirred under nitrogen at room temperature for 20 h. Diethyl ether was added and the mixture filtered through a pad of silica. The filtrate was evaporated in vacuo and the crude product purified by flash chromatography on silica, eluting with ethyl acetate/heptane (0:10 to 2:8), to yield the title compound.

Workup

  1. filtrationthe mixture filtered through a pad of silica
  2. customThe filtrate was evaporated in vacuo
  3. customthe crude product purified by flash chromatography on silica
  4. washeluting with ethyl acetate/heptane (0:10 to 2:8)

Sources & evidence

ORD record
ord-d190b5b277d9426eb593d99b862e2d10
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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