Dichloromethane → 3-Butyn-1-ol, 4-(4-fluorophenyl)-, 1-methanesulfonate

HRID 2057644Notes

Reaction equation

HRID 2057644 reaction equation
ClCCl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(N(CC)CC)C>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][CH2:13][CH2:14][O:15][S:17]([CH3:16])(=[O:19])=[O:18])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 124784404-(4-Fluorophenyl)but-3-yn-1-ol

Product 1

HCID 203313013-Butyn-1-ol, 4-(4-fluorophenyl)-, 1-methanesulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 250 ml. of dichloromethane, 25 g. 4-(4-fluorophenyl)-3-butyn-1-ol and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil.

Workup

  1. additionTo a mixture of 250 ml
  2. additionis added dropwise, over 15 minutes
  3. temperatureThe mixture is cooled at -10° C. to -15° C. for 30 minutes
  4. washwashed with 300 ml
  5. dry with materialThe organic layer is dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil

Sources & evidence

ORD record
ord-a7f7e5bc18fb4f43858395fd4ba95d27
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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