Water → HCID 54389814, compound

HRID 486968Notes

Reaction equation

HRID 486968 reaction equation
[H-].[Na+].[C:3]1([OH:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl[CH2:15][CH2:16][C@@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].O>CN(C=O)C>[C:3]1([O:13][CH2:15][CH2:16][C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[OH:18])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 70051-NaphtholHCID 24758Sodium hydrideHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanol

Product 1

HCID 54389814HCID 54389814, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
5 °C

Procedure

To a mixture of 8 ml of DMF and 0.44 g of 60% sodium hydride in mineral oil at 5° C. in an ice bath was added dropwise a solution of 1.44 g of 1-naphthol in 8 ml of DMF. The reaction mixture was stirred at 5° C. for two hours and a solution of 1.71 g of (S)-(-)-3-chloro-1-phenyl-1-propanol in 5 ml of DMF was added. After stirring overnight at room temperature, the reaction mixture was poured into 150 ml of water and extracted with ethyl acetate (3×50 ml). The combined extracts were combined and washed with water and 1N sodium hydroxide solution and dried over sodium sulfate. Yield: 2.56 g (92%). The crude product can be recrystallized from 95:5 hexane/ethyl acetate to give 1.5 g (54%) of purified (S)-(+)-3-(1-naphthalenyloxy)-1-phenyl-1-propanol, mp 76°-78° C.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washwashed with water and 1N sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. customThe crude product can be recrystallized from 95:5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-42bd86c252904e7898392f8f6a2211c5
Source dataset
uspto-grants-1994_03
Patent number
US05292962

Reaction notes

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