Thiophenol → HCID 14856380, compound

HRID 1089565Notes

Reaction equation

HRID 1089565 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]([O:13][C:14]1[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]2[O:21][CH:20]([CH2:22]Br)[CH2:19][C:18]=2[C:24]=1[CH3:25])(=[O:12])[CH3:11]>CN(C)C=O.O>[C:10]([O:13][C:14]1[C:15]([CH3:27])=[C:16]([CH3:26])[C:17]2[O:21][CH:20]([CH2:22][S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:19][C:18]=2[C:24]=1[CH3:25])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 14856379HCID 14856379, compound

Product 1

HCID 14856380HCID 14856380, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of thiophenol [425 mg (3.8 mmol)] in dimethylformamide (10 ml) was added, under ice-cooling, sodium hydride [167 mg (4.2 mmol, content:60%)]. To the reaction mixture was added, after stirring for 20 minutes, a solution of 5-acetoxy-2-bromomethyl-4,6,7-trimethyl-2,3-dihydrobenzofuran [1.2 g (3.8 mmol)] dimethylformamide (5 ml). The mixture was stirred for further 30 minutes. The reaction mixture was diluted with water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried and concentrated. The concentrate was crystallized from isopropylether-hexane to afford 5-acetoxy-4,6,7-trimethyl-2-phenylthiomethyl-2,3-dihydrobenzofuran (Compound 4) [1.2 g (yield : 91.3%)]. In a manner as above, compounds 2, 6, 8, 10, 12 and 18 were synthesized by employing the corresponding thio compounds (3-mercaptopropionic acid, 1-octanethiol, 2-mercaptopyridine, 4-fluorothiophenol, 2-naphthalene thiol and benzyl mercaptan). Incidentally, when 3-mercaptopropionic acid was employed as the starting compound, 2.2 equivalents of sodium hydride was used.

Workup

  1. temperaturecooling
  2. additionTo the reaction mixture was added
  3. stirringThe mixture was stirred for further 30 minutes
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe extract solution was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe concentrate was crystallized from isopropylether-hexane

Sources & evidence

ORD record
ord-d7445f1572874a259ddb32f6abfb39c2
Source dataset
uspto-grants-1990_10
Patent number
US04966973

Reaction notes

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