Formic Acid → Methyl 3-methyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2H-1-benzofuran-6-carboxylate

HRID 1602692Notes

Reaction equation

C(N(CCCC)CCCC)CCC.C(O)=O.I[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH:29]=[C:30]([C:32]1[CH:41]=[CH:40][C:39]2[C:38]([CH3:43])([CH3:42])[CH2:37][CH2:36][C:35]([CH3:45])([CH3:44])[C:34]=2[CH:33]=1)[CH3:31]>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:31][C:30]1([C:32]2[CH:41]=[CH:40][C:39]3[C:38]([CH3:43])([CH3:42])[CH2:37][CH2:36][C:35]([CH3:45])([CH3:44])[C:34]=3[CH:33]=2)[C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH2:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of tributylamine (0.5 ml, 2.1 mmol), palladium diacetate (0.03 g, 0.2 mmol), formic acid (0.06 ml, 1.3 mmol) and methyl 4-iodo-3-[2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl]-1-propenyloxy]benzoate (0.65 g, 1.3 mmol) in acetonitrile (10 ml) is heated at 60° C. for 4 h. The reaction medium is concentrated on a rotary evaporator under vacuum at 40° C. 20 ml of water and 20 ml of ethyl ether are added. After separation of the phases by settling, the organic phase is washed twice with 20 ml of water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C.

Workup

concentrationThe reaction medium is concentrated on a rotary evaporator under vacuum at 40° C
addition20 ml of water and 20 ml of ethyl ether are added
customAfter separation of the phases
washthe organic phase is washed twice with 20 ml of water
dry with materialdried over magnesium sulphate
concentrationconcentrated on a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record: ord-3c0e9178303f4171857d737ceb9a9416
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981776

Reaction notes

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