Hydrochloric Acid → HCID 69310779, compound

HRID 898425Notes

Reaction equation

HRID 898425 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH:19]=[CH:20][C:21](OCC)=[O:22].C(O)(C)C.Cl>C1COCC1.CCOCC.O>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH:19]=[CH:20][CH2:21][OH:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 21226445Aluminium lithium hydrideHCID 74067277HCID 74067277, compound

Product 1

HCID 69310779HCID 69310779, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (480 mg, 12.6 mmol) was slurried in anhydrous THF (15 mL) and treated with dropwise addition of a solution of 3-(5-methyl-2-phenyloxazol-4-yl)-acrylic acid, ethyl ester (2.60 g, 10.1 mmol) at 0° C. The reaction mixture was stirred for 1.5 h at this temperature and then treated with dropwise addition of isopropanol (1.0 mL) followed by water (10 mL). The biphasic suspension was acidified with 0.1 N HCl (10 mL), diluted with ether (20 mL) and partitioned. The aqueous layer was extracted once with ether (15 mL) and the combined organic layers dried over MgSO4 and concentrated to provide a colorless oil (1.13 g, 52%): Rf=0.18 (50% hexanes/EtOAc); 1H NMR (300 MHz, CDCl3) δ 7.99-8.03 (m, 2H), 7.42-7.48 (m, 3H), 6.60 (dt, 1H), 6.47 (d, 1H), 4.35 (m, 2H), 3.76 (b, 1H), 2.37 (s, 3H); MS(EI): 216 (M+1).

Workup

  1. custompartitioned
  2. extractionThe aqueous layer was extracted once with ether (15 mL)
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-33884d2f3d9c4dc1b1eff0296fd22b96
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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