Imidazole → (+/-)-1-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol

HRID 13912Notes

Reaction equation

HRID 13912 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:22])[CH2:20][OH:21])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]([CH2:18][CH:19]([OH:22])[CH2:20][O:21][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68583597(+/-)-3-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol

Product 1

HCID 68582701(+/-)-1-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-olYield 73.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-3-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]propane-1,2-diol (9.10 g, 30.5 mmol) in N,N-dimethylformamide (150 mL) was added tert-butyldimethylsilyl chloride (4.83 g, 32.04 mmol) followed by imidazole (2.49 g, 36.60 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was quenched with methanol (5 mL) and diluted with diethyl ether (500 mL). The organic layer was washed with aqueous hydrogen chloride (200 mL, 0.5 N), water (3×200 mL), saturated aqueous sodium chloride (200 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to provide a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:4) gave 9.20 g (73%) of (±)-1-[4-(benzyloxy)-2,3-dihydro-1H-inden-5-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ol as a colorless oil. Rf=0.37 (silica, ethyl acetate:hexanes 1:4); Anal. calcd. for C25H36O3Si: C, 72.77; H, 8.79. Found: C, 72.3; H, 8.48.

Workup

  1. customThe reaction mixture was quenched with methanol (5 mL)
  2. additiondiluted with diethyl ether (500 mL)
  3. washThe organic layer was washed with aqueous hydrogen chloride (200 mL, 0.5 N), water (3×200 mL), saturated aqueous sodium chloride (200 mL)
  4. dry with materialdried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customto provide a crude oil
  7. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:4)

Sources & evidence

ORD record
ord-11922663de0f478ca6073f697c013ba7
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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