Hydrochloric Acid → HCID 2793910, compound

HRID 1814273Notes

Reaction equation

HRID 1814273 reaction equation
[BH4-].[Na+].[C:3]1([CH2:13][C:14](=[O:17])[CH2:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl>CO>[C:3]1([CH2:13][CH:14]([OH:17])[CH2:15][CH3:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 4564544HCID 4564544, compound

Product 1

HCID 2793910HCID 2793910, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (1.80 g, 47.4 mmol) was added portion wise at 0° C. to a solution of 1-naphthyl-2-butanone (4.70 g, 23.7 mmol) in CH3OH (100 mL). The mixture was stirred at 0° C. for 3 h. A solution of 1 N HCl (10 mL) was added, and the solvent was removed in vacuo. Water (50 mL) was added to the residue, and the aqueous was extracted with EtOAc (300 mL). The combined organic extracts were washed with the H2O (100 mL) and brine (50 mL), and the solvent was removed by rotary evaporation. Silica gel flash chromatography (10% EtOAc in hexanes) yielded 4.10 g (86%) of 1-naphthalen-1-ylmethyl-propanol as a colorless oil: 1H-NMR (400 MHz, CDCl3) δ 8.04 (dd, 1 H), 7.85 (dd, 1 H), 7.74 (dd, 1 H), 7.54-7.43 (m, 2 H), 7.41-7.24 (m, 2 H), 3.93-3.87 (m, 1 H), 3.36 (dd, 1 H), 3.05 (dd, 1H), 1.71-1.57 (m, 2 H), 1.45 (br s, 1 H), 1.05 (t, 3 H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionWater (50 mL) was added to the residue
  3. extractionthe aqueous was extracted with EtOAc (300 mL)
  4. washThe combined organic extracts were washed with the H2O (100 mL) and brine (50 mL)
  5. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-f3bbe790afa345a2a86a5c92433c3af7
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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