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

HRID 1071819Notes

Reaction equation

HRID 1071819 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, CDC13) 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-dad11043b89a41b18f86249f600d1da5
Source dataset
uspto-grants-2005_06
Patent number
US06906155B1

Reaction notes

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