Hydrochloric Acid → HCID 178448035, compound

HRID 1109956Notes

Reaction equation

HRID 1109956 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1C=O.[I-].[CH2:15]([C@H:18]1[CH2:23][CH2:22][C@H:21]([C@H:24]2[CH2:29][CH2:28][C@H:27]([CH2:30][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:26][CH2:25]2)[CH2:20][CH2:19]1)[CH2:16][CH3:17].[CH3:50]C(C)([O-])C.[K+].Cl>C1COCC1.O>[F:13][C:2]([F:1])([F:12])[O:3][C:4]1[CH:5]=[CH:8][C:9]([CH:50]=[CH:30][C@H:27]2[CH2:26][CH2:25][C@H:24]([C@H:21]3[CH2:20][CH2:19][C@H:18]([CH2:15][CH2:16][CH3:17])[CH2:23][CH2:22]3)[CH2:29][CH2:28]2)=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27771922-(Trifluoromethoxy)benzaldehydeHCID 23665647Potassium tert-butoxideHCID 178448074HCID 178448074, compound

Product 1

HCID 178448035HCID 178448035, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

95 g of trifluoromethoxybenzaldehyde in 150 ml of THF are added over the course of 2-3 hours at -10° to -5° to a mixture of 300 g of trans-4-(trans-4-propylcyclohexyl)cyclohexylmethyltriphenylphosphonium iodide, 56 g of potassium tert.-butoxide and 500 ml of THF. The mixture is allowed to warm to room temperature and neutralized using 2 N HCl, water is added, and the mixture is extracted with methyl tert.-butyl ether. After work-up of the organic phase and purification by chromatography on silica gel, 1-(4-trifluoromethoxyphenyl)-2-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]ethene is obtained.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with methyl tert.-butyl ether
  3. customAfter work-up of the organic phase and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-af80fe3c22bb4fc5bbb85d361dd528d3
Source dataset
uspto-grants-1994_06
Patent number
US05324449

Reaction notes

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