Allyl chloride → HCID 15405343, compound

HRID 1952706Notes

Reaction equation

HRID 1952706 reaction equation
[OH-].[K+].[C:3]([C:5]1([OH:15])[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6]1)#[CH:4].[CH2:16](Cl)[CH:17]=[CH2:18]>CO.CC(O)C.CC(OC)(C)C.Cl[Cu].C([O-])([O-])=O.[K+].[K+]>[C:3]([C:5]1([OH:15])[CH2:14][CH2:13][CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6]1)#[C:4][CH2:18][CH:17]=[CH2:16]

Participants

9

Reactant 3

HCID 7850Allyl chlorideHCID 14797Potassium HydroxideHCID 15405342HCID 15405342, compound

Product 1

HCID 15405343HCID 15405343, compoundYield 90%

Reagents, catalysts & solvents 5

HCID 11430Potassium CarbonateCatalystHCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of KOH (7.93 g), K2CO3 (1.08 g) and CuCl (0.72 g) in MeOH (40 ml) cooled to 0° C. and kept under N2 was added dropwise a solution of 7-ethynyl-spiro[4.5]decan-7-ol (2) (16.80 g, 94.4 mmol) in iPrOH (40 ml). The resulting red-brown mixture was stirred another 20 minutes at 0° C., then was treated with allylchlorid (11.6 ml, 141.6 mmol, 1.5 equiv) added dropwise for 10 mn, warmed to room temperature and left under stirring at room temperature overnight. The mixture was diluted with MTBE (200 ml), washed with saturated NH4Cl (2×40 ml), H2O (3×30 ml) until neutral pH and dried over MgSO4. 18.52 g (90%) of crude product (3) was isolated as an orange oil that was used without further purification in the final step.

Workup

  1. additionadded dropwise for 10 mn
  2. temperaturewarmed to room temperature
  3. waitleft
  4. stirringunder stirring at room temperature overnight
  5. washwashed with saturated NH4Cl (2×40 ml), H2O (3×30 ml) until neutral pH
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-a80da877504841ed87a6d68f2677bf80
Source dataset
uspto-grants-2000_09
Patent number
US06114300

Reaction notes

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