Water → 7-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanol

HRID 1584339Notes

Reaction equation

HRID 1584339 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](OCC)=[O:30])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 21224419Ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 212244947-[3-Methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanoate (9.6 g) in tetrahydrofuran (THF) (50 ml) was added dropwise, at room temperature, to a suspension of lithium aluminum hydride (0.96 g) in tetrahydrofuran (THF) (50 ml). The mixture was stirred for 30 minutes at room temperature, to which was then added, under ice-cooling, water (6 ml). Insolubles were filtered off, then the filtrate was concentrated. The concentrate was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (2:3), was obtained 7-[3-methoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]heptanol, which was recrystallized from chloroform-ether to give colorless needles, m.p.78-79° C.

Workup

  1. additionwas then added, under ice-
  2. temperaturecooling
  3. filtrationInsolubles were filtered off
  4. concentrationthe filtrate was concentrated
  5. washFrom the fraction eluted with ethyl acetate-hexane (2:3)

Sources & evidence

ORD record
ord-0eb1b82170234bfdbf6957670fc32560
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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