Water → HCID 6430550, compound

HRID 1010515Notes

Reaction equation

HRID 1010515 reaction equation
[CH3:1][C:2]([CH3:16])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[O:13].O>C1COCC1>[CH3:16][CH:2]([CH2:3][CH2:4][CH2:5]/[C:6](/[CH3:15])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:14])=[CH:11]/[CH:12]=[O:13])[CH3:1]

Participants

4

Reactant 2

HCID 962WaterHCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

Product 1

HCID 6430550HCID 6430550, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.53 g of 2 in 150 mL of dry THF in a round-bottom flask equipped with a water-cooled condenser was added a solid mixture of 31.04 g of NiCl2.6H2O and 4.27 g of Al powder (caution: exothermic). The reaction mixture was stirred at room temperature for 6 h. The solid mass was removed by filtration, and the solvent was dried over MgSO4 and removed by rotary evaporation, which afforded 0.50 g of racemic 3, predominantly the (E)-isomer. 1H NMR δ (ppm) 9.8 (t, CHO), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.3 (m, CH2C(CH3)═CH), 2.2-2.4 (qd, CH2CHO), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.2-1.5 (m, CH2CH(CH3)CH2CO), 0.9 (d, CH2C(CH3)═CH).

Workup

  1. temperaturecooled condenser
  2. additionwas added
  3. customThe solid mass was removed by filtration
  4. dry with materialthe solvent was dried over MgSO4
  5. customremoved by rotary evaporation, which
  6. customafforded 0.50 g of racemic 3

Sources & evidence

ORD record
ord-ce2d9b09433745d6b36e00064bcdf3a0
Source dataset
uspto-grants-2011_07
Patent number
US07977315B2

Reaction notes

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