Water → HCID 67155832, compound

HRID 409510Notes

Reaction equation

HRID 409510 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH:19]([C:20]([O:22][CH3:23])=[O:21])[C:18](=[O:24])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[BH4-].[Na+].O>O1CCCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH:19]([C:20]([O:22][CH3:23])=[O:21])[CH:18]([OH:24])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67155857HCID 67155857, compound

Product 1

HCID 67155832HCID 67155832, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(benzo[d][1,3]dioxol-5-yl)-4-oxochroman-3-carboxylate (58 mg, 178 μmol) in tetrahydrofuran (1.0 mL) was diluted with methanol (2.0 mL) and stirred on an ice/acetone bath. Sodium borohydride (7 mg, 178 μmol) was added and the resulting mixture was stirred for 40 min. After this time, water (about 10 mL) was added and the mixture was stirred while warming to rt. The resulting white solid was collected by filtration, washed with water and dried under vacuum to provide racemic methyl 2-(benzo[d][1,3]dioxol-5-yl)-4-hydroxychroman-3-carboxylate (51 mg, 87%). 1H NMR (400 MHz, CDCl3) δ ppm 2.69 (s, 1 H) 3.47 (dd, J=6.6, 2.5 Hz, 1 H) 3.51 (s, 3 H) 5.25 (d, J=5.6 Hz, 1 H) 5.31 (d, J=2.5 Hz, 1 H) 5.99 (s, 2 H) 6.82 (d, J=8.1 Hz, 1 H) 6.89 (d, J=8.1 Hz, 1 H) 6.92 (m, 2 H) 7.03 (t, J=7.4 Hz, 1 H) 7.23 (td, J=7.1, 1.0 Hz, 1 H) 7.57 (d, J=7.6 Hz, 1 H). Mass spectrum m/z 351.20 (M+Na)+.

Workup

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

Sources & evidence

ORD record
ord-1563860bb7bd49caa7ba2e38a037612e
Source dataset
uspto-grants-2014_06
Patent number
US08759390B2

Reaction notes

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