2-Methylbenzaldehyde → HCID 69965728, compound

HRID 989262

Reaction equation

HRID 989262 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O([Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])S(C(F)(F)F)(=O)=O.[Li]CCCC.CCCCCC.[CH3:54][C:55]1[CH:62]=[CH:61][CH:60]=[CH:59][C:56]=1[CH:57]=O>C1COCC1>[C:39]([Si:36]([CH3:38])([CH3:37])[O:8][C:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3](=[CH:54][C:55]2[CH:62]=[CH:61][CH:60]=[CH:59][C:56]=2[CH3:57])[CH:2]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

7

Reactant 5

HCID 107222-MethylbenzaldehydeHCID 11776TriphenylphosphineHCID 707232-Cyclohepten-1-oneHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 178418244HCID 178418244, compound

Product 1

HCID 69965728HCID 69965728, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cycloheptenone (71.7 mmol) in 220 ml of anhydrous THF there are added, in succession, triphenylphosphine (72.6 mmol) and then, dropwise, tert-butyldimethylsilyl triflate (72.3 mmol), and the whole is stirred at room temperature for 1 hour 30 minutes. The mixture is then brought to −78° C., and a solution of nBuLi/hexane (72 mmol) is added slowly, followed 30 minutes later by 2-methylbenzaldehyde (72.03 mmol). The whole is stirred at that temperature for 30 minutes, and then with the temperature gradually returning to room temperature. After 2 hours 30 minutes, the reaction mixture is precipitated from 2.5 liters of petroleum ether and filtered, and the filtrate is concentrated to dryness. The title product is purified by chromatography over silica gel (100% heptane).

Workup

  1. customis then brought to −78° C.
  2. customgradually returning to room temperature
  3. waitAfter 2 hours 30 minutes
  4. customthe reaction mixture is precipitated from 2.5 liters of petroleum ether
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness
  7. customThe title product is purified by chromatography over silica gel (100% heptane)

Sources & evidence

ORD record
ord-1998a41d3c444e92befe8253cdc01e54
Source dataset
uspto-grants-2003_10
Patent number
US06638962B2

Linked notes

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