Sodium ethanethiolate → HCID 22905871, compound

HRID 1488580Notes

Reaction equation

HRID 1488580 reaction equation
[S-:1][CH2:2][CH3:3].[Na+].[C:5]([C:9]1[C:14]2[O:15][CH2:16][C:17]([CH3:19])([CH3:18])[C:13]=2[CH:12]=[C:11]([C:20](=[O:23])[CH2:21]Cl)[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>CO>[C:5]([C:9]1[C:14]2[O:15][CH2:16][C:17]([CH3:19])([CH3:18])[C:13]=2[CH:12]=[C:11]([C:20](=[O:23])[CH2:21][S:1][CH2:2][CH3:3])[CH:10]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 4459711Sodium ethanethiolateHCID 10612804HCID 10612804, compound

Product 1

HCID 22905871HCID 22905871, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium thioethoxide (0.54 g, 6.4 mmol) is added in portions to a solution of 1 -(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-2-chloroethan-1-one (1.12 g, 4.0 mmol) in 30 mL of methanol at room temperature. The reaction is stirred for 2.5 h, and concentrated in vacuo. The residue is dissolved in ether, washed with water and with brine, dried over anhydrous magnesium sulfate, and concentrated to give 1.12 g of the crude product. Purification by flash column chromatography on silica gel (5% ethyl acetate-hexane) afforded 0.72 g of the title compound as a light yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in ether
  3. washwashed with water and with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give 1.12 g of the crude product
  7. customPurification by flash column chromatography on silica gel (5% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e8f225b7a6944726a2b736d19c936b91
Source dataset
uspto-grants-1997_10
Patent number
US05674891

Reaction notes

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