Chloroform → HCID 70284007, compound

HRID 362267Notes

Reaction equation

HRID 362267 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH2:11][C:12]#[C:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)=[CH:5][CH:4]=1.C(Cl)(Cl)Cl.[OH-:26].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[S:9][CH2:11][CH:12]([C:13](=[O:26])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 57257102HCID 57257102, compound

Product 1

HCID 70284007HCID 70284007, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NMR analysis of both gums indicated the second to be of higher purity, so this was used in the subsequent stages. A mixture of the crude 1-(4-methoxyphenylsulphinyl)-4-phenoxybut-2-yne (2.1 g) and chloroform (25 ml) was heated under nitrogen at an external temperature of 80°-85° C. for 1 hour, allowed to stand at ambient temperature for 18 hours, and heated at an external temperature of 90°-95° C. for 6 hours. The solvent was removed by distillation to leave crude 5-methoxy-3-methylene-2-phenoxymethyl-2,3-dihydrobenzo[b]thiophen-2-ol as an orange gum. The orange gum was dissolved in dichloromethane (30 ml) and the solution was shaken vigorously for a few seconds with 5M aqueous sodium hydroxide solution (25 ml), then the organic solution was separated, washed with water (25 ml), dried (MgSO4), and the solvent removed in vacuo to leave crude 1-(5-methoxy-2,3-dihydrobenzo[b]thiophen-3-yl)-2-phenoxyethanone as a red gum (1.94 g) which was used without purification.

Workup

  1. temperaturewas heated under nitrogen at an external temperature of 80°-85° C. for 1 hour
  2. temperatureheated at an external temperature of 90°-95° C. for 6 hours
  3. customThe solvent was removed by distillation
  4. customto leave crude 5-methoxy-3-methylene-2-phenoxymethyl-2,3-dihydrobenzo[b]thiophen-2-ol as an orange gum
  5. customthe organic solution was separated
  6. washwashed with water (25 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-de2406ebbd3f4d7683b4ca546a0ad1c6
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

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