Dimethyl Sulfide → HCID 58390780, compound

HRID 1015667Notes

Reaction equation

HRID 1015667 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:12]=1[CH:13]=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC.P([O-])(O)(O)=[O:25].[Na+].Cl([O-])=O.[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][C:12]=1[C:13]([OH:25])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 58390720HCID 58390720, compound

Product 1

HCID 58390780HCID 58390780, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-Formyl-5-phenyl-thiophene-2-carboxylic acid tert-butyl ester (300 mg, 1.04 mmol) in dry THF (20 ml), at 0° C., under nitrogen, was treated with methyl sulfide (10% w/w in THF, 3.8 ml, 5.2 mmol) followed by sodium dihydrogenphosphate (30% aqueous solution, 9.56 ml, 2.05 mmol). After 0.5 h, the solution was treated with sodium chlorite (30% w/w aqueous solution, 1.9 ml, 2.08 mmol) added over 1 min via a syringe. The pale yellow solution was stirred for 1.5 h at 0° C., then diluted with water (20 ml) and extracted with EtOAc (4×40 ml). The aqueous phase was separated, extracted with more EtOAc (40 ml) and the combined extracts were washed with brine dried and concentrated to give 316 mg (100%) of 5-Phenyl-thiophene-2,3-dicarboxylic acid 2-tert-butyl ester as a pale brown solid. NMR 1H (CD3CO; 400 MHz): 7.87 (s, 1H); 7.83-7.81 (m, 2H); 7.17-7.53 (m, 3H); 1.65 (bs, 9H).

Workup

  1. additionadded over 1 min via a syringe
  2. extractionextracted with EtOAc (4×40 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with more EtOAc (40 ml)
  5. washthe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca13a19a775f4caabacad8889a11b586
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

Loading…