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

HRID 1075632Notes

Reaction equation

C(N(CCCC)CCCC)CCC.C(O)=O.[Br:17][C:18]1[S:22][C:21]([C:23]([CH2:25][O:26][C:27]2[C:36](I)=[CH:35][C:34]3[C:33]([CH3:39])([CH3:38])[CH2:32][CH2:31][C:30]([CH3:41])([CH3:40])[C:29]=3[CH:28]=2)=[CH2:24])=[CH:20][CH:19]=1>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Br:17][C:18]1[S:22][C:21]([C:23]2([CH3:24])[CH2:25][O:26][C:27]3[CH:28]=[C:29]4[C:34](=[CH:35][C:36]2=3)[C:33]([CH3:39])([CH3:38])[CH2:32][CH2:31][C:30]4([CH3:41])[CH3:40])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tributylamine (2.66 ml, 18.39 mmol), palladium diacetate (53 mg, 0.24 mmol), formic acid (0.205 ml, 5.32 mmol) and 5-bromo-2-[1-(3-iodo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yloxymethyl)-vinyl]thiophene (2.57 mg, 4.84 mmol) in acetonitrile (75 ml) was heated at 60° C. for 4 h. The reaction medium was concentrated in a rotary evaporator under vacuum at 40° C. Water and ethyl ether were added. After decantation, the organic phase was washed twice with 20 ml of 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
additionWater and ethyl ether were added
washAfter decantation, the organic phase was washed twice with 20 ml of water
dry with materialdried over magnesium sulfate
concentrationconcentrated in a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record: ord-d1e9daf60348409786e96e2ac14f8a23
Source dataset: uspto-grants-1999_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05905088

Reaction notes

Loading…