Sodium borohydride → HCID 86603464, compound

HRID 1171014Notes

Reaction equation

HRID 1171014 reaction equation
[CH3:1][C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:14]=2)=[C:10]([CH3:26])[CH:9]=[C:8]([OH:27])[C:3]=1[C:4](OC)=[O:5].[BH4-].[Na+]>C(O)C.O>[CH3:1][C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[C:15]([CH:23]([CH3:24])[CH3:25])[CH:14]=2)=[C:10]([CH3:26])[CH:9]=[C:8]([OH:27])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86603463HCID 86603463, compound

Product 1

HCID 86603464HCID 86603464, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2,4-dimethyl-6-hydroxy-3-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzoate in ethanol-water (3.0 mL, 95:5) at room temperature was added NaBH4. The reaction mixture was heated at 80° C. for 4 h and cooled to room temperature. The reaction mixture was quenched with aqueous NH4Cl and extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with 30% acetone in hexanes to afford 2,4-dimethyl-6-hydroxy-3-(4′-methoxymethoxy-3′-iso-propylbenzyl)benzyl alcohol: 1H NMR (300 MHz, CD3OD): δ 6.97 (d, J=2.4 Hz, 1 H), 6.92 (d, J=13.2 Hz, 1 H), 6.68 (dd, J=13.2, 2.4 Hz, 1 H), 6.59 (s, 1 H), 5.17 (s, 2 H), 4.78 (s, 2 H), 3.96 (s, 2 H), 3.47 (s, 3 H), 3.30 (m, 1 H), 2.24 (s, 3 H), 2.19 (s, 3 H), 1.18 (d, J=10.8 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=acetone-hexanes (3:7); Rf=0.40.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was quenched with aqueous NH4Cl
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with 30% acetone in hexanes

Sources & evidence

ORD record
ord-9f08ed62f3e04632a01f44b0fb9db20b
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

Loading…