Tetrahydrofuran → HCID 136375571, compound

HRID 2396076Notes

Reaction equation

HRID 2396076 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[O:17][C:18]([CH3:25])=[C:19]([CH2:21]C(O)=O)[N:20]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CON=C=[N:30][C:31](C)(C)C.C1C[O:38]CC1.CCCCCC.C[CH2:47][O:48][C:49](C)=[O:50]>>[CH3:47][O:48][C:49](=[O:50])[NH:30][C:31](=[O:38])[CH2:21][C:19]1[N:20]=[C:16]([C:7]2[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=2)[O:17][C:18]=1[CH3:25]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 18988327HCID 18988327, compoundHCID 21226206Ethyl acetate hexaneHCID 135422986HCID 135422986, compound

Product 1

HCID 136375571HCID 136375571, compoundYield 94%

Procedure

A mixture of [2-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methyloxazol-4-yl]-acetic acid (2.0 g, 5.8 mmol), N-methoxy-N'-tert-butylcarbodiimide (0.9 g, 5.8 mmol) prepared according to Bull. Chem. Soc. Japan 45, 3607-3611 (1972) and THF (20 mL) was refluxed for 6 hours. The volatiles were removed in vacuo, andthe residue was purified by flash chromatography on acid washed silica gel (5% H3PO4 in MeOH), eluting solvent: hexane/EtOAc 3/1, to give an off-white solid (2.2 g, 94% yield), m.p. 125°-127° C.

Workup

  1. customprepared
  2. customThe volatiles were removed in vacuo
  3. customandthe residue was purified by flash chromatography on acid
  4. washwashed silica gel (5% H3PO4 in MeOH)
  5. washeluting solvent

Sources & evidence

ORD record
ord-931d29a89ddc4edc8629c32f008fb5ad
Source dataset
uspto-grants-1996_02
Patent number
US05491159

Reaction notes

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