Tetrahydrofuran → (2S,3S)-2-benzyloxy-5-(1-naphthyl)pentan-3-ol

HRID 278483Notes

Reaction equation

HRID 278483 reaction equation
[CH2:1]([O:8][C@@H:9]([CH3:12])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]1([CH2:23][CH2:24]Br)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[Mg].C1COCC1>CCOCC.[Br-].[Zn+2].[Br-]>[CH2:1]([O:8][C@H:9]([C@@H:10]([OH:11])[CH2:24][CH2:23][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 1395411-(2-Bromoethyl)naphthaleneHCID 5462224MagnesiumHCID 11116387(2S)-2-(Benzyloxy)propanal

Product 1

HCID 57094200(2S,3S)-2-benzyloxy-5-(1-naphthyl)pentan-3-olYield 30.8%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
4 °C

Procedure

A solution of (S)-2-(benzyloxy)propanal (Bull. Chem. Soc. Jpn. (1989) 62, 3038, 16.25 g) in ether (200 ml) was added to a suspension of zinc bromide (26.75 g) in ether (50 ml) below 6° C. and then an ethereal solution of 2-(1-naphthyl)ethylmagnasium bromide, prepared from 2-(1-naphthyl)ethyl bromide (46.55 g) and magnesium turnings (9.63 g) in ether (300 ml), was added below 8° C. The mixture was stirred at 4° C. for 1 h and then THF (200 ml) was added. The final mixture was stirred overnight at room temperature. After cooling, the mixture was quenched with saturated aqueous ammonium chloride solution (200 ml) and insoluble material was filtered. The filtrate was extracted with ethyl acetate and the extract was washed with brine, dried and concentrated in vacuo. Flash chromatography (hexane:ethyl acetate =9:1) gave (2S,3S)-2-benzyloxy-5-(1-naphthyl)pentan-3-ol (9.78 g, 30.8%) as an oil.

Workup

  1. additionwas added below 8° C
  2. temperatureAfter cooling
  3. customthe mixture was quenched with saturated aqueous ammonium chloride solution (200 ml) and insoluble material
  4. filtrationwas filtered
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7515fca575774954a6359403eb49c13a
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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