Hydrochloric Acid → 7-Hydroxymethyl-4-phenylcoumarin

HRID 21574Notes

Reaction equation

HRID 21574 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=3)[O:10][C:9](=[O:20])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC(Cl)=O)C(C)C.[BH4-].[Na+].Cl>C1COCC1.O.CCN(CC)CC>[OH:18][CH2:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9](=[O:20])[O:10]2)=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 15780556HCID 15780556, compound

Product 1

HCID 157805577-Hydroxymethyl-4-phenylcoumarin

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-phenyl-7-coumarincarboxylic acid from Step 4 (550 mg) and Et3N (560 μL) in THF (25 mL) at 0° C. was added isobutylchloroformate (560 μL) dropwise. After 45 min., NaBH4 (185 mg) in H2O was added and stirring continued for a further 20 min. The mixture was poured onto 1N HCl, extracted 3×Et2O, dried and evaporated. Chromatography on silica gel using hexane/EtOAc 1:1 afforded the title compound as a solid.

Workup

  1. waitcontinued for a further 20 min
  2. extractionextracted 3×Et2O
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-7f41e9a9881f4fde83ac8ce21e15cca1
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Reaction notes

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