Water → HCID 18665548, compound

HRID 2395382Notes

Reaction equation

HRID 2395382 reaction equation
C1COCC1.[C:6]1([C@H:12]2[CH2:16][O:15][C:14]([C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[O:20][CH2:21][C:22](OCC)=[O:23])=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Li+].[BH4-].O>C(OCC)C>[C:6]1([C@H:12]2[CH2:16][O:15][C:14]([C:17]3[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=3)[O:20][CH2:21][CH2:22][OH:23])=[N:13]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 18665566HCID 18665566, compound

Product 1

HCID 18665548HCID 18665548, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a THF (40 ml) solution of ethyl 3-(4,5-dihydro-4(S)-phenyloxazol-2-yl)phenoxyacetate (2.77 g, 8.5 mmol) was added LiBH4 (0.37 g, 17 mmol) in one portion. After stirring for 4 h, water (40 ml) was added and the mixture diluted with diethyl ether (40 ml). The aqueous layer was separated and extracted with ethyl acetate (3×20 ml). The combined organic extracts were washed with 0.5 N aqueous HCl (20 ml), brine (20 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (=2:1) to afford title compound (0.95 g, 40%) as a colorless liquid.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. washThe combined organic extracts were washed with 0.5 N aqueous HCl (20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (=2:1)

Sources & evidence

ORD record
ord-18ab21ba3a98429b8ad3ce840a3cf8f2
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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