Water → HCID 10241494, compound

HRID 257205Notes

Reaction equation

HRID 257205 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:14])[O:9][C:8]2[CH:10]=[CH:11][S:12][C:7]=2[C:6](=[O:13])[CH2:5]1.O>C(O)C>[OH:13][CH:6]1[CH2:5][C:4]([CH3:14])([CH3:3])[O:9][C:8]2[CH:10]=[CH:11][S:12][C:7]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 15643884129969-30-8

Product 1

HCID 10241494HCID 10241494, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.97 g, 25.5 mmol) was added to a solution of 5,6-dihydro-5,5-dimethyl-7H-thieno [3,2-b]pyran-7-one (3.1 g, 17.0 mmol) in ethanol (50 mL) and stirred at rt for 2 h. An additional 0.97 g of sodium borohydride was added and the mixture was stirred 16 h. The mixture was poured into water and extracted with dichloromethane. The dichloromethane solution was washed with water (5×) and dried over magnesium sulfate. The solvent was evaporated in vacuo to give the product, 2.96 g (95%), as a brown oil: IR (neat): 3373, 2976, 1561 and 1400 cm-1 ; MS: m/z 185 (MH+); 1H NMR (CDCl3): δ 1.34 (s, 3H), 1.45 (s, 3H), 1.87 (m, 1H), 1.94 (d, J=7.0 Hz, 1H, exchanges with D2O), 2.16 (m, 1H), 4.88 (m, 1H), 6.57 (d, J=5.4 Hz, 1H), 7.13 (d, J=5.4 Hz, 1H). This oil was used without further purification in the next step.

Workup

  1. stirringthe mixture was stirred 16 h
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane solution was washed with water (5×)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customto give the product, 2.96 g (95%)
  7. customThis oil was used without further purification in the next step

Sources & evidence

ORD record
ord-c8fe3c1e58c349949d38d8668ad0eef3
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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