Tetrahydrofuran → 2-(1H-Inden-2-yl)ethan-1-ol

HRID 1269366Notes

Reaction equation

HRID 1269366 reaction equation
ClC[SiH2][C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C1C[O:16][CH2:15][CH2:14]1>>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:4]1[CH2:14][CH2:15][OH:16]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 131724997HCID 131724997, compound

Product 1

HCID 143166262-(1H-Inden-2-yl)ethan-1-olYield 33.4%

Conditions

Temperature
-78 °C

Procedure

Under nitrogen flow, a 1 L three-necked flask receives 400 mL of THF and 8 g of 2-chloromethylsilylindene and the mixture is cooled to −78° C. To this, 38.5 mL (38.5 mmol) of a solution (1.0M) of LiN(trimethylsilylene)2 in THF is added dropwise. After stirring at room temperature for 15 hours, the solvent is distilled off and the residue is extracted with 300 mL of hexane. The solvent was distilled off to obtain 2.2 g (6.4 mmol) of (1,2′-dimethylsilylene)(2,1′-dimethylsilylene) (indene) 2 (yield:33.4%). The results of 1H-NMR analysis (90 MHz, CDCl3) are as follows: δ-0.69, 0.73 (12H, dimethylsilylene), 3.66 (4H, —CH2—), 7.17 (8H, Ar—H).

Workup

  1. distillationthe solvent is distilled off
  2. extractionthe residue is extracted with 300 mL of hexane
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-081424588ee646bfb3bd8dd425c86f89
Source dataset
uspto-grants-2007_04
Patent number
US07199202B2

Reaction notes

Loading…