Hydrochloric Acid → HCID 178448035, compound

HRID 1735361Notes

Reaction equation

HRID 1735361 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 2N 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-027c61e505484026a1e5f8b82a9ddc05
Source dataset
uspto-grants-1996_07
Patent number
US05536442

Reaction notes

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