Chlorotrimethylsilane → 9,9-Bis(trimethylsilyloxymethyl)fluorene

HRID 2416161Notes

Reaction equation

HRID 2416161 reaction equation
[OH:1][CH2:2][C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.C(N(CC)CC)C.[CH3:25][Si:26](Cl)([CH3:28])[CH3:27]>ClCCl>[CH3:25][Si:26]([CH3:28])([CH3:27])[O:1][CH2:2][C:3]1([CH2:16][O:17][Si:26]([CH3:28])([CH3:27])[CH3:25])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 3450229H-Fluorene-9,9-dimethanol

Product 1

HCID 226390959,9-Bis(trimethylsilyloxymethyl)fluoreneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 9,9-bis(hydroxymethyl)fluorene (4.4 mmol) was admixed with 20 ml of dichloromethane. The mixture was cooled in ice-water bath, and 1.9 ml of triethyl amine (13.2 mmol) was added thereto. Then 1.4 ml of trimethylsilyl chloride (11 mmol) was added drop-wise, and the mixture was stirred in ice-water bath for further 2 hours. The reaction mixture was washed with water, and the organic layer separated was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.14 g of concentrate (yield 88%). MS (EI) m/e: 370(M+).

Workup

  1. washThe reaction mixture was washed with water
  2. customthe organic layer separated
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated
  6. customto give 1.14 g
  7. concentrationof concentrate (yield 88%)

Sources & evidence

ORD record
ord-78e4067b2d3c41a0bb13847dce85ba20
Source dataset
uspto-grants-2004_11
Patent number
US06822109B2

Reaction notes

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