Sodium ethanethiolate → HCID 22905871, compound

HRID 2257259Notes

Reaction equation

HRID 2257259 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-c06700878dd7418d92c58b555c51c860
Source dataset
uspto-grants-1997_08
Patent number
US05656661

Reaction notes

Loading…