Sodium borohydride → (4-phenyl-1H-isochromen-3-yl)methanol

HRID 634367Notes

Reaction equation

HRID 634367 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][O:9][C:8]=2[CH:17]=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][O:9][C:8]=2[CH2:17][OH:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118131333HCID 118131333, compound

Product 1

HCID 118131349(4-phenyl-1H-isochromen-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-phenyl-1H-isochromene-3-carbaldehyde (Intermediate G21, 410 mg, 1.735 mmol) suspended in MeOH (1 ml) was added dropwise to a solution of sodium tetrahydroborate (65.7 mg, 1.735 mmol) in MeOH (17.3 ml) at RT. The mixture was partitioned between AcOEt/NH4Cl 5% (2 ml/2 ml), the organic phase was separated, anhydrified over Na2SO4 and evaporated in vacuo to give a crude that underwent next step without any further purification.

Workup

  1. customThe mixture was partitioned between AcOEt/NH4Cl 5% (2 ml/2 ml)
  2. customthe organic phase was separated
  3. customevaporated in vacuo
  4. customto give a crude that underwent next step
  5. customwithout any further purification

Sources & evidence

ORD record
ord-8ec13868633c4562bdc57bb16adebe21
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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