Ethanethiol → HCID 18423661, compound

HRID 2270117Notes

Reaction equation

HRID 2270117 reaction equation
[H-].[Na+].C(S)C.C[O:7][C:8]1[C:16]2[O:15][C:14]([CH:17]3[CH2:21][CH2:20][O:19][CH2:18]3)=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1>>[O:19]1[CH2:20][CH2:21][CH:17]([C:14]2[O:15][C:16]3[C:8]([OH:7])=[CH:9][CH:10]=[CH:11][C:12]=3[CH:13]=2)[CH2:18]1

Participants

4

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 18423637HCID 18423637, compound

Product 1

HCID 18423661HCID 18423661, compoundYield 79.1%

Conditions

Temperature
140 °C

Procedure

Sodium hydride (0.19 g, 60% in mineral oil) was added to a stirred solution of ethane thiol (0.34 ml) in N,N-dimethylformramide (6 ml) at room temperature under a dry nitrogen atmosphere. After stirring for 15 minutes 7-methoxy-2-(tetrahydrofuran-3-yl)-benzofuran (0.5 g) in N,N-dimethylfornamide (6 ml) was added and the reaction heated to 140° C. for 2 hours. After cooling to room temperature the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic extract was dried over magnesium sulphate, filtered and preadsorbed onto silica. Purification by column chromatography on silica eluting with 50% ethyl acetate in heptane afforded the title compound as a brown oil (0.37 g).

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas removed in vacuo
  4. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulphate
  7. filtrationfiltered
  8. customPurification by column chromatography on silica eluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-4da1490844da4efd8ea17dede85c31e1
Source dataset
uspto-grants-2001_12
Patent number
US06331556B2

Reaction notes

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