Water → HCID 18546136, compound

HRID 1857531Notes

Reaction equation

HRID 1857531 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](OCC)=[O:24])=[CH:17][C:15]=2[N:16]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][OH:24])=[CH:17][C:15]=2[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 18546144HCID 18546144, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18546136HCID 18546136, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 3-[2-(2-naphthylmethyl)-benzoxazol-5-yl]propionate (5.8 g) in ether (100 ml)-tetrahydrofuran (100 ml) was added lithium aluminum hydride (0.73 g), and the mixture was stirred at room temperature for one hour. To the reaction mixture was added water (4 ml). Insolubles were filtered off. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1, v/v), 3-[2-(2-naphthylmethyl)benzoxazol-5-yl]propanol (2.1 g, 41%) was obtained. Recrystallization from dichloromethane-isopropylether gave colorless prisms. Melting point: 102-103° C.

Workup

  1. filtrationInsolubles were filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. washFrom the fraction eluted with ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-77927b4a725e4a40804c5dee4ecc1382
Source dataset
uspto-grants-2000_11
Patent number
US06147099

Reaction notes

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