HCID 389880, compound → HCID 10516051, compound

HRID 983774Notes

Reaction equation

HRID 983774 reaction equation
[Br-].[C:2]1(C([PH3+])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.[C:27]([C:32]([C:41]([O:43][CH2:44][CH3:45])=[O:42])([CH2:38][CH:39]=[CH2:40])[CH2:33][CH2:34][C:35](=O)[CH3:36])([O:29][CH2:30][CH3:31])=[O:28]>C1COCC1>[CH2:38]([C:32]([CH2:33][CH2:34][C:35]([CH3:2])=[CH2:36])([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:39]=[CH2:40]

Participants

5

Reactant 3

HCID 389880HCID 389880, compoundHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 10516051HCID 10516051, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a THF suspension (4.2 ml) containing triphenylmethylphosphonium bromide (0.536 g, 1.5 mmol) was added dropwise at 0° C. butyl lithium (1.4 mmol in 0.88 ml of 1.6M hexane solution). The reaction liquid was stirred at 0° C. for 30 minutes and then given 5,5-dicarboethoxy-7-octen-2-on (0.27 g, 1.0 mmol), followed by stirring at 0° C. for 1 hour. After treatment and purification as in Referential Example 9, there was obtained 0.239 g of diethyl allyl(3-methyl-3-butenyl)malonate (yields: 89%). Characteristic Values of allyl(3-methyl-3-butenyl)malonate

Workup

  1. customThe reaction liquid
  2. stirringby stirring at 0° C. for 1 hour
  3. customAfter treatment and purification as in Referential Example 9

Sources & evidence

ORD record
ord-f6e0f2e3342946799c5b503b9119ba60
Source dataset
uspto-grants-2005_03
Patent number
US06867161B1

Reaction notes

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