Water → HCID 18546136, compound

HRID 1267323Notes

Reaction equation

HRID 1267323 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-eee51d367f214235b45cabdb676bb0f3
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

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