Formic Acid → Methyl [5-(3,5,5,8,8-pentamethyl-2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-3-yl)-thiophene-3-yl]carboxylate

HRID 1075627Notes

Reaction equation

C(N(CCCC)CCCC)CCC.C(O)=O.I[C:18]1[C:19]([O:32][CH2:33][C:34]([C:36]2[S:40][CH:39]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:37]=2)=[CH2:35])=[CH:20][C:21]2[C:22]([CH3:31])([CH3:30])[CH2:23][CH2:24][C:25]([CH3:29])([CH3:28])[C:26]=2[CH:27]=1>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:35][C:34]1([C:36]2[S:40][CH:39]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:37]=2)[CH2:33][O:32][C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][C:18]1=2)[C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23][C:22]3([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tributylamine (3.64 ml, 25.16 mmol), palladium diacetate (74 mg, 0.33 mmol), formic acid (0.28 ml, 7.28 mmol) and methyl 5-[1-(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxymethyl)-vinyl]-3-thiophenecarboxylate (3.38 g, 6.62 mmol) in acetonitrile (100 ml), was heated at 60° C. for 4 h. The reaction medium was concentrated in a rotary evaporator under vacuum at 40° C., treated with water and extracted with ethyl ether. After decantation, the organic phase was washed twice with water, dried over magnesium sulfate and concentrated in a rotary evaporator under vacuum at 40° C.

Workup

concentrationThe reaction medium was concentrated in a rotary evaporator under vacuum at 40° C.
additiontreated with water
extractionextracted with ethyl ether
washAfter decantation, the organic phase was washed twice with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record: ord-fa538e44417245d39b991eea6948e786
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905088

Reaction notes

Loading…