Aluminium lithium hydride → HCID 12412168, compound

HRID 2164139Notes

Reaction equation

HRID 2164139 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:28]=[CH:27][C:11]2[S:12][C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14]([CH2:15][C:16](OCC)=[O:17])[C:10]=2[CH:9]=1>C(OCC)C>[Cl:7][C:8]1[CH:28]=[CH:27][C:11]2[S:12][C:13]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:14]([CH2:15][CH2:16][OH:17])[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22750368HCID 22750368, compound

Product 1

HCID 12412168HCID 12412168, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 11.5 parts by weight of lithium aluminum hydride in 100 parts by volume of refluxing ethyl ether under a nitrogen atmosphere is added over a 0.25 hour addition period 25.0 parts by weight of ethyl 5-chloro-2-phenylbenzo[b]thiophene-3-acetate in 100 parts by volume of ethyl ether. The resulting mixture is heated at reflux temperature for 48 hours before cooling to 0° C. and quenching with cautious sequential addition of 11.5 parts by volume of water, 11.5 parts by volume of 15% aqueous sodium hydroxide solution and 34.5 parts by volume of water. The reaction mixture is stirred for an additional two hours at 0° C. before the granular aluminum salts are removed by vacuum filtration. The aluminum salts are then washed with a liberal amount of ethyl ether. Concentration of the filtrate in vacuo affords 5-chloro-2-phenylbenzo[b]thiophene-3-ethanol as an off-white solid material. This material is represented by the following structural formula ##STR14##

Workup

  1. additionis added over a 0.25 hour
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux temperature for 48 hours
  4. customquenching with cautious sequential addition of 11.5 parts by volume of water, 11.5 parts by volume of 15% aqueous sodium hydroxide solution and 34.5 parts by volume of water
  5. customare removed by vacuum filtration
  6. washThe aluminum salts are then washed with a liberal amount of ethyl ether

Sources & evidence

ORD record
ord-fb4cc06d363c4531b0e4d489e3aea4d4
Source dataset
uspto-grants-1979_01
Patent number
US04137414

Reaction notes

Loading…