Hydrochloric Acid → HCID 178455783, compound

HRID 1765008Notes

Reaction equation

HRID 1765008 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]#[CH:11].C[Mg+].[Br-].[CH2:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH:23]=[O:24])[CH2:19][CH2:18]1)[CH3:16].Cl>O1CCCC1>[CH2:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH:23]([OH:24])[C:11]#[C:10][C:3]2[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=2[F:1])[CH2:19][CH2:18]1)[CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 231157211-Ethynyl-2,3,4-trifluorobenzeneHCID 178418689HCID 178418689, compoundHCID 178455781HCID 178455781, compound

Product 1

HCID 178455783HCID 178455783, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Into the tetrahydrofuran (THF) (100 ml) solution containing 2,3,4-trifluorophenylacetylene (20 g), the THF solution (93 ml) of 1.5 M bromide methyl magnesium was added dropwise at 0° C., and stirred for 1 hour. Into this, the THF (50 ml) solution of trans-4-ethylcyclohexane carboaldehyde (18 g) was added dropwise, and stirred for 1 hour. The reaction solution was poured into 5% hydrochloric acid, extracted with ethyl acetate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 1-(trans-4-ethylcyclohexyl)-3-(2,3,4-trifluorophenyl)-2-propyne-1-ol (38 g).

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-719b4ec4b66e43f7bf61286d9365d337
Source dataset
uspto-grants-2007_06
Patent number
US07226644B2

Reaction notes

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