Sodium borohydride → HCID 67546737, compound

HRID 2089490Notes

Reaction equation

HRID 2089490 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH2:5][S:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[CH2:5][S:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67547360HCID 67547360, compound

Product 1

HCID 67546737HCID 67546737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-oxo-isothiochroman-7-carbonitrile (830 mg, 4.4 mmol) in methanol (25 mL) at 0° C. is added NaBH4 (330 mg, 8.8 mmol). The reaction is permitted to stir for 1 hour and then quenched with 1N aqueous HCl. The reaction is concentrated to approximately half of its original volume and diluted with ethyl acetate. The organic layer is separated, dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-hexanes, 0:1 to 1:1) to afford 4-hydroxy-isothiochroman-7-carbonitrile; MS: (ESI) m/z 192.1 (M+H)+.

Workup

  1. customquenched with 1N aqueous HCl
  2. concentrationThe reaction is concentrated to approximately half of its original volume
  3. additiondiluted with ethyl acetate
  4. customThe organic layer is separated
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-hexanes, 0:1 to 1:1)

Sources & evidence

ORD record
ord-34f7871f775d45aa863426965006176f
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…