Formic Acid → HCID 19612294, compound

HRID 1602708Notes

Reaction equation

C(N(CCCC)CCCC)CCC.C(O)=O.C([O-])=O.[Na+].C1OCCOCCOCCOCCOC1.I[C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][C:38]=1[O:47][CH:48]=[C:49]([C:51]1[C:60]([CH3:61])=[CH:59][C:58]2[C:57]([CH3:63])([CH3:62])[CH2:56][CH2:55][C:54]([CH3:65])([CH3:64])[C:53]=2[CH:52]=1)[CH3:50]>C(#N)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[CH3:61][C:60]1[C:51]([C:49]2([CH3:50])[C:37]3[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][C:38]=3[O:47][CH2:48]2)=[CH:52][C:53]2[C:54]([CH3:65])([CH3:64])[CH2:55][CH2:56][C:57]([CH3:63])([CH3:62])[C:58]=2[CH:59]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of tributylamine (0.4 ml, 0.88 mmol), palladium diacetate (0.017 g, 0.083 mmol), formic acid (0.034 ml, 0.91 mmol), sodium formate (60 mg, 0.88 mmol), 15-crown-5 and methyl 4-iodo-3-[2-(3-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propenyloxy]benzoate (429 mg, 0.83 mmol) in acetonitrile (10 ml) is heated at 45° C. for 8 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-a498e0eebd5140eaba7f4d699a7ec314
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981776

Reaction notes

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