Tetrahydrofuran → 10H-phenothiazine-3-methanol, 10-methyl-

HRID 355418Notes

Reaction equation

HRID 355418 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH3:19])[C:10]3[C:15]([S:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:4].C1COCC1>C(O)C>[OH:4][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH3:19])[C:10]3[C:15]([S:16][C:17]=2[CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 61782610-Methyl-10H-phenothiazine-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 63853310H-phenothiazine-3-methanol, 10-methyl-Yield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With ice-cooling, sodium borohydride (4.16 g, 110 mmol) was added to a mixture of 3-formyl-10-methylphenothiazine (24.6 g, 102 mmol), THF (100 ml) and ethanol (100 ml), the mixture was stirred for 10 minutes and then at room temperature for 20 minutes. The solvent was evaporated under a reduced pressure, water and 2N hydrochloric acid were added to the residue in that order, and then the reaction product was extracted with ethyl acetate. The extract was washed with a saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure. By recrystallizing the resulting residue from ethyl acetate-hexane, the title compound (18.9 g, 77.7 mmol, 76%) was obtained as yellow crystals.

Workup

  1. temperatureWith ice-cooling
  2. waitat room temperature for 20 minutes
  3. customThe solvent was evaporated under a reduced pressure, water and 2N hydrochloric acid
  4. additionwere added to the residue in that order
  5. extractionthe reaction product was extracted with ethyl acetate
  6. washThe extract was washed with a saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution in that order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under a reduced pressure
  9. customBy recrystallizing the resulting residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5e62b552beaa4212900bd4664683f5ce
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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