Water → HCID 18546136, compound

HRID 1377660Notes

Reaction equation

HRID 1377660 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-953e5d5e218e4f78ad987436f6c62c5d
Source dataset
uspto-grants-1997_09
Patent number
US05665748

Reaction notes

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