4-(4,5-Dihydro-1,3-oxazol-2-yl)phenol → HCID 490094, compound

HRID 1197863Notes

Reaction equation

HRID 1197863 reaction equation
OC1C=CC(C2OCCN=2)=CC=1.[Cl:13][C:14]1[S:15][C:16]([C:19](=O)[CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[O:32][CH2:33][CH2:34][N:35]=3)=[CH:27][CH:26]=2)=[CH:17][CH:18]=1>>[Cl:13][C:14]1[S:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[O:32][CH2:33][CH2:34][N:35]=3)=[CH:27][CH:26]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 1012874-(4,5-Dihydro-1,3-oxazol-2-yl)phenolHCID 490090HCID 490090, compound

Product 1

HCID 490094HCID 490094, compound

Procedure

A solution of 2-chloro-5-(5-chloropentanoyl)thiophene (3c) (1.18 g, 0.005 mol) and aluminum trichloride (0.66 g, 0.005 mol) in anhydrous ethyl ether (40 ml) and tetrahydrofuran (30 ml) was slowly added to a mixture, cooled to 0°-5° C., consisting of lithium and aluminium hydride (1.33 g, 0.01 mol) in anhydrous ethyl ether (40 ml). The reaction mixture was magnetically stirred for 6 hrs. at 30°-40° C., cooled to 0°-5° C., and cautiously diluted with water (20 ml) and 6N hydrogen sulphate (20 ml). The organic phase was separated, washed with water, and dried on anhydrous sodium sulphate. Solvent removal gave a chromatographically pure liquid residue (TCL: silicon dioxide-cyclohexane) consisting of 7 (0.99 g; 89%), which was directly used in the subsequent reaction with 2-(4-hydroxyphenyl)-4,5-dihydro-oxazole, as described for the preparation of 4c, to give 9 (0.81 g; 52%) (after crystallization via cycloexane). M.p. 99°-100° C. Anal. (C18H20ClNO2S).

Workup

  1. customto give
  2. custom9 (0.81 g; 52%) (after crystallization via cycloexane)

Sources & evidence

ORD record
ord-d0ba594619754a30a441893b056f0cb4
Source dataset
uspto-grants-1994_01
Patent number
US05278184

Reaction notes

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