Water → 4-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-one

HRID 1650215Notes

Reaction equation

HRID 1650215 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].C(N(CC)CC)C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>ClCCl>[Si:19]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-hydroxy-1-indanone (594 mg) and triethylamine (0.7 ml) in dry dichloromethane (10 ml) was added tert-butyldimethylsilyl chloride (724 mg) in several portions at 0° C. The mixture was stirred overnight at ambient temperature and then poured into a mixture of water (30 ml) and dichloromethane (20 ml). The separated organic layer was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate solution, succeedingly. The solution was dried and evaporated in vacuo. The residue was purified by columnchromatography on silica gel eluted by dichloromethane to give 4-(tert-butyldimethylsilyl)oxy-1-indanone (1.002 g) as an oil.

Workup

  1. washThe separated organic layer was washed with 1N-hydrochloric acid, brine and aqueous saturated sodium bicarbonate solution
  2. customThe solution was dried
  3. customevaporated in vacuo
  4. customThe residue was purified by columnchromatography on silica gel
  5. washeluted by dichloromethane

Sources & evidence

ORD record
ord-41eb3fbbbaf141eebd609e7746d3e75d
Source dataset
uspto-grants-1990_05
Patent number
US04923881

Reaction notes

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