Hydrochloric Acid → 3-{[3-(Triethoxysilyl)propyl]thio}-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

HRID 732852Notes

Reaction equation

HRID 732852 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5].[SH:15][CH2:16][CH2:17][CH2:18][Si:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[CH2:21]([O:20][Si:19]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])[CH2:18][CH2:17][CH2:16][S:15][CH:2]([CH3:1])[CH2:3][C:4]([CH:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][CH2:9][CH:8]=[C:7]1[CH3:14])=[O:5])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 846581-Propanethiol, 3-(triethoxysilyl)-HCID 5366077(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)but-2-en-1-one

Product 1

HCID 688158943-{[3-(Triethoxysilyl)propyl]thio}-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of α-damascone (9.60 g; 50.0 mmol) and 3-mercaptopropyltriethoxysilane (95% pure, 12.52 g, 50.0 mmol) in THF (40 ml) was treated with DBU (1.52 g, 10.0 mmol) and stirred at 40° C. for 90 min. The reaction solution was treated with 5% HCl, extracted twice with ether, washed with water, saturated aqueous NaHCO3 and then with saturated aqueous NaCl, dried over Na2SO4 and concentrated at 70° C./0.01 mbar. The reaction yielded 21.2 g (99%). of crude product:

Workup

  1. extractionextracted twice with ether
  2. washwashed with water, saturated aqueous NaHCO3
  3. dry with materialwith saturated aqueous NaCl, dried over Na2SO4
  4. concentrationconcentrated at 70° C./0.01 mbar
  5. customThe reaction yielded 21.2 g (99%)

Sources & evidence

ORD record
ord-ddfef09fcf28429baee08345b17bdbd2
Source dataset
uspto-grants-2009_09
Patent number
US07589055B2

Reaction notes

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