Chlorotrimethylsilane → 9-Methoxymethyl-9-trimethylsilyloxymethyl-fluorene

HRID 2416160Notes

Reaction equation

HRID 2416160 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.C(N(CC)CC)C.[CH3:26][Si:27](Cl)([CH3:29])[CH3:28]>ClCCl>[CH3:1][O:2][CH2:3][C:4]1([CH2:17][O:18][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol

Product 1

HCID 226391279-Methoxymethyl-9-trimethylsilyloxymethyl-fluoreneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.2 mmol) was dissolved in 20 ml of dichloromethane. The solution was cooled in ice-water bath, and 0.7 ml of triethyl amine (5 mmol) was added thereto. After stirring for 5 minutes, 0.6 ml of trimethylsilyl chloride (4.6 mmol) was added drop-wise, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. 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 1.41 g of concentrate (yield 86%). MS(EI)m/e: 312(M+).

Workup

  1. stirringthe mixture was stirred for further 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. washThe reaction mixture was washed with water
  4. customthe organic layer separated
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated
  8. customto give 1.41 g
  9. concentrationof concentrate (yield 86%)

Sources & evidence

ORD record
ord-a216e12047ba45cd936dac7dcb5fe07b
Source dataset
uspto-grants-2004_11
Patent number
US06822109B2

Reaction notes

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