Carbon Tetrachloride → 2-Chloromethyl-4-(beta-trimethylsilylethoxymethoxy)-naphthalene

HRID 1004941Notes

Reaction equation

HRID 1004941 reaction equation
[CH3:1][Si:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]([CH2:18]O)[CH:9]=1.C(#N)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:45]>>[Cl:45][CH2:18][C:10]1[CH:9]=[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:21])([CH3:20])[CH3:1])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 11776Triphenylphosphine2×HCID 22126553[4-(2-Trimethylsilyl-ethoxymethoxy)-naphthalen-2-yl]-methanol

Product 1

HCID 221265292-Chloromethyl-4-(beta-trimethylsilylethoxymethoxy)-naphthaleneYield 63%

Conditions

Temperature
0 °C

Procedure

23.72 g (77.91 mmol) of [4-(2-trimethylsilyl-ethoxymethoxy)-naphthalen-2-yl]-methanol were dissolved in 350 ml of carbon tetrachloride and the solution was cooled to 0° C. Thereupon, 350 ml of acetonitrile and 26.54 g (1.012 mmol) of triphenylphosphine were added. The light yellow solution was stirred at 0° C. for 30 minutes, warmed to room temperature and stirred for a further 2 hours. A further 10.14 g (38.7 mmol) of triphenylphosphine were added and the reaction mixture was stirred at room temperature for 90 minutes. Subsequently, the mixture was partitioned between methylene chloride and water, the organic phase was dried over magnesium sulphate and finally the solvent was removed under reduced pressure. The crude product was chromatographed on silica gel using a 3:7 mixture of methylene chloride and hexane as the eluent. There were obtained 15.81 g (63% of theory) of 2-chloromethyl-4-(β-trimethylsilylethoxymethoxy)-naphthalene as a light yellow oil; MS: 322, 324 (M)+.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for a further 2 hours
  3. stirringthe reaction mixture was stirred at room temperature for 90 minutes
  4. customSubsequently, the mixture was partitioned between methylene chloride and water
  5. dry with materialthe organic phase was dried over magnesium sulphate
  6. customfinally the solvent was removed under reduced pressure
  7. customThe crude product was chromatographed on silica gel using
  8. additiona 3:7 mixture of methylene chloride and hexane as the eluent

Sources & evidence

ORD record
ord-808e6641539f413487b6e869b8e357b6
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

Loading…