Sodium borohydride → Methyl 2-(3,4-dichlorophenyl)-4-hydroxychroman-3-carboxylate

HRID 409517Notes

Reaction equation

HRID 409517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:18]([C:19]([O:21][CH3:22])=[O:20])[C:17](=[O:23])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:18]([C:19]([O:21][CH3:22])=[O:20])[CH:17]([OH:23])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67155790Racemic methyl 2-(3,4-dichlorophenyl)-4-oxochroman-3-carboxylate

Product 1

HCID 67155590Methyl 2-(3,4-dichlorophenyl)-4-hydroxychroman-3-carboxylateYield 89.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of racemic methyl 2-(3,4-dichlorophenyl)-4-oxochroman-3-carboxylate (100 mg, 285 μmol) in THF (2.0 mL) was diluted with methanol (4.0 mL) and stirred on an ice/acetone bath. Sodium borohydride (11 mg, 285 μmol) was added and the resulting mixture was stirred for 40 min. After this time, the mixture was diluted with water and stirred while warming to rt. The resulting white solid was collected by filtration, washed with water and dried under vacuum to provide methyl 2-(3,4-dichlorophenyl)-4-hydroxychroman-3-carboxylate (90 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.49 (s, 3 H) 3.51 (m, 1 H) 5.26 (d, J=6.1 Hz, 1 H) 5.35 (d, J=2.5 Hz, 1 H) 6.94 (dd, J=8.1, 1.0 Hz, 1 H) 7.06 (td, J=7.6, 1.0 Hz, 1 H) 7.22-7.29 (m, 2 H) 7.47 (d, J=8.6 Hz, 1 H) 7.56 (d, J=1.5 Hz, 1 H) 7.58 (d, J=7.6 Hz, 1 H).

Workup

  1. stirringthe resulting mixture was stirred for 40 min
  2. stirringstirred
  3. filtrationThe resulting white solid was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e800df1ce7f54d0d9f591e6b4d9c2e41
Source dataset
uspto-grants-2014_06
Patent number
US08759390B2

Reaction notes

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