Water → 2-(3-Methoxy-4-propoxy-5-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-tetrahydrofuran

HRID 341850Notes

Reaction equation

P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:30](O)[CH2:31][CH2:32][CH:33]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[OH:34])[CH:20]=[C:21]([N+:27]([O-:29])=[O:28])[C:22]=1[O:23][CH2:24][CH2:25][CH3:26].O>N1C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:30]2[CH2:31][CH2:32][CH:33]([C:35]3[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=3)[O:34]2)[CH:20]=[C:21]([N+:27]([O-:29])=[O:28])[C:22]=1[O:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of P4S10 (19.25 g, 43.3 mmol) in 250 mL of pyridine was heated at 120° C. for 75 minutes. To this suspension was then added a solution of 1-(3-methoxy-4-propoxy-5-nitrophenyl) -4-(3,4,5-trimethoxyphenyl)-butane-1,4-diol (4.65 g, 10 mmol) in 50 mL of pyridine. The temperature was reduced to 90° C. and stirring continued for an additional 90 minutes. After cooling, ice and water were added, the mixture was extracted with methylene chloride. The organic layer was washed with water, 5% HCl, water, sodium bicarbonate and saturated aqueous sodium chloride, and then dried over magnesium sulfate, filtered and evaporated.

Workup

customwas reduced to 90° C.
temperatureAfter cooling
extractionthe mixture was extracted with methylene chloride
washThe organic layer was washed with water, 5% HCl, water, sodium bicarbonate and saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-dace04c62b9e4c6d86e74200bb2b1436
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856323

Reaction notes

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