Water → HCID 10241494, compound

HRID 981488Notes

Reaction equation

HRID 981488 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 (5x) 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 (5x)
  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-73b3ca218bed4fccb20d658de52af2cb
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

Loading…