Sodium borohydride → Methyl 5,8-dimethyl-4-hydroxy-6-thiochromanecarboxylate

HRID 378812Notes

Reaction equation

HRID 378812 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[C:4](=[O:17])[CH2:5][CH2:6][S:7]2.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([CH3:16])=[C:8]2[C:3]=1[CH:4]([OH:17])[CH2:5][CH2:6][S:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21696595Methyl 5,8-dimethyl-4-oxo-6-thiochromanecarboxylate

Product 1

HCID 21696591Methyl 5,8-dimethyl-4-hydroxy-6-thiochromanecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.40 g (0.04 mol) of methyl 5,8-dimethyl-4-oxo-6-thiochromanecarboxylate were dissolved in 200 ml of ethanol and, a little at a time, admixed with 0.89 g (0.023 mol) of sodium borohydride. The mixture was subsequently stirred at room temperature for another 1 h and then concentrated using a rotary evaporator. The residue was taken up in 200 ml of ethyl acetate, washed with sat. NaCl solution (2×100 ml), dried over MgSO4 and concentrated using a rotary evaporator.

Workup

  1. concentrationconcentrated
  2. customa rotary evaporator
  3. washwashed with sat. NaCl solution (2×100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-d39a6c0d503f4ce693e3fa5b8686b5db
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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