Tri(butyl)vinyltin → methyl 3-allyl-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2H-1-benzofuran-6-carboxylate

HRID 1602701Notes

Reaction equation

[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.I[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=1[O:27][CH:28]=[C:29]([C:31]1[CH:40]=[CH:39][C:38]2[C:37]([CH3:42])([CH3:41])[CH2:36][CH2:35][C:34]([CH3:44])([CH3:43])[C:33]=2[CH:32]=1)[CH3:30]>C(#N)C>[CH2:30]([C:29]1([C:31]2[CH:40]=[CH:39][C:38]3[C:37]([CH3:42])([CH3:41])[CH2:36][CH2:35][C:34]([CH3:43])([CH3:44])[C:33]=3[CH:32]=2)[C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH2:28]1)[CH:1]=[CH2:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of palladium bis(triphenylphosphine)diacetate (0.15 g, 0.2 mmol), tributylvinyltin (0.56 ml, 1.92 mmol) and methyl 4-iodo-3-[2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl]-1-propenyloxy]benzoate (1 g, 1.99 mmol) in acetonitrile (20 ml) is heated at 80° C. for 3 days, adding tributylvinyltin (0.28 ml, 0.96 mmol) every 24 h. The reaction medium is concentrated on a rotary evaporator under vacuum at 40° C. 40 ml of water and 40 ml of ethyl ether are added. After separation of the phases by settling, the organic phase is washed twice with 40 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
addition40 ml of water and 40 ml of ethyl ether are added
customAfter separation of the phases
washthe organic phase is washed twice with 40 ml of water
dry with materialdried over magnesium sulphate
concentrationconcentrated on a rotary evaporator under vacuum at 40° C.

Sources & evidence

ORD record: ord-12d3c508cffe4242a741dc950a634199
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981776

Reaction notes

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