Dimethylformamide → HCID 15547440, compound

HRID 324178Notes

Reaction equation

C(S)C.CN(C=O)C.[H-].[Na+].[C:11]([C:15]1[C:16]([CH3:38])([CH3:37])[CH2:17][O:18][C:19]=1[C:20]1[CH:34]=[C:33]([O:35]C)[C:23]2[N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:26][C:22]=2[CH:21]=1)([CH3:14])([CH3:13])[CH3:12]>O>[C:11]([C:15]1[C:16]([CH3:38])([CH3:37])[CH2:17][O:18][C:19]=1[C:20]1[CH:34]=[C:33]([OH:35])[C:23]2[N:24]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:26][C:22]=2[CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 155 °C

Procedure

In nitrogen atmosphere at 0° C., 0.25 mL of ethanethiol was added to 3 mL of DMF dissolving 104 mg (2.6 mmol) of 60% sodium hydride. Adding 505 mg (1.3 mmol) of 4-t-butyl-5-(4-methoxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [62]), the mixture was refluxed for 1.0 hours at 155° C. The resulting mixture was poured in pure water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried with magnesium sulfate anhydride, and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=5:1) to obtain 410 mg of 4-t-butyl-5-(4-hydroxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [63]). Yield 82.8%.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated aqueous solution of sodium chloride
dry with materialdried with magnesium sulfate anhydride
concentrationconcentrated
washthe elution
additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-01ee4932d5ac4c0ab66883bddff88e3f
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218135B1

Reaction notes

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