Ammonium Chloride → HCID 19793917, compound

HRID 867913Notes

Reaction equation

HRID 867913 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][OH:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH:13]([Mg]Br)=[CH2:14].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:11]([OH:12])[CH:13]=[CH2:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27240201-(p-Chlorophenyl)cyclopropanemethanolHCID 178418507HCID 178418507, compound

Product 1

HCID 19793917HCID 19793917, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirred solution of 1-(4-chlorophenyl)-1-cyclopropanemethanol (1.8 g) in dry tetrahydrofuran (60 ml) at -78° C. is added IM vinylmagnesium bromide (12 ml) in tetrahydrofuran over 10 mins. The mixture is then allowed to warm to -20° C. and saturated aqueous ammonium chloride added (30 ml). The mixture is concentrated under reduced pressure, and extracted with ether (x3). The combined extracts are dried and the solvent evaporated under reduced pressure to the required compound, 3 g, nD 1.5523.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. extractionextracted with ether (x3)
  3. customThe combined extracts are dried
  4. customthe solvent evaporated under reduced pressure to the required compound, 3 g, nD 1.5523

Sources & evidence

ORD record
ord-eee3537c5e3e40d39a8498a604d678c1
Source dataset
uspto-grants-1988_10
Patent number
US04777185

Reaction notes

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