HCID 14832882, compound → HCID 14832888, compound

HRID 2165985Notes

Reaction equation

HRID 2165985 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]1[C:28]3[C:23](=[CH:24][C:25]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:27]=3)[CH:22]=[C:21](Br)[C:20]=1[O:38][CH3:39])=[C:14]([O:40][CH3:41])[C:13](Br)=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:43]1([Mg]Br)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CCOCC>[CH2:1]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]1[C:28]3[C:23](=[CH:24][C:25]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:27][CH2:26][CH2:25][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=3)[CH:22]=[C:21]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C:20]=1[O:38][CH3:39])=[C:14]([O:40][CH3:41])[C:13]([C:10]1[CH:9]=[CH:18][CH:17]=[CH:16][CH:11]=1)=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

4

Reactant 2

HCID 14832882HCID 14832882, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 14832888HCID 14832888, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 80 mg of Ni[PPh3 ]2Cl2 and 20 ml of ether were added to 1.9 g of Compound 3, and stirred for 15 minutes in a nitrogen atmosphere. 10 mmol of phenylmagnesium bromide were added and refluxed for 4 hours. After cooling down, the solution was quenched with 20 ml of 1N hydrochloric acid and extracted with chloroform. The organic layer was evaporated under reduced pressure, and purified with column chromatography (silica gel, hexane/benzene) to get 670 mg of pure 6,6'-dioctadecyl-3,3'-diphenyl-2,2'-dimethoxy-1,1'-binaphthyl. (yield 36%) (Compound 4).

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureAfter cooling down
  3. customthe solution was quenched with 20 ml of 1N hydrochloric acid
  4. extractionextracted with chloroform
  5. customThe organic layer was evaporated under reduced pressure
  6. custompurified with column chromatography (silica gel, hexane/benzene)

Sources & evidence

ORD record
ord-3a63020ec04d48f98995af0768bb9b89
Source dataset
uspto-grants-1990_07
Patent number
US04942149

Reaction notes

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