Triethylamine → HCID 13638465, compound

HRID 2169194Notes

Reaction equation

HRID 2169194 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([O:4][CH2:3][C:2]([CH3:1])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219535beta,beta-Dimethylbenzeneethanol

Product 1

HCID 13638465HCID 13638465, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-2-phenylpropan-1-ol (51) (8.5 g, 56.6 mmol, Eq: 1.00) was stirred in dichloromethane (90.4 ml) at 0° C., triethylamine (6.87 g, 9.46 ml, 67.9 mmol, Eq: 1.2) and then methanesulfonyl chloride (7.13 g, 4.82 ml, 62.2 mmol, Eq: 1.1) were added over 3 minutes. The reaction mixture was stirred at 0° C. for 30 minutes, removed from the ice bat h and allowed to warm to room temperature and stirred for 15 hours. The reaction mixture was diluted with dichloromethane, washed with water, saturated sodium bicarbonate, and brine, and dried with magnesium sulfate. The solvent was removed on a rotary evaporator to give 2-methyl-2-phenylpropyl methanesulfonate (52) as a clear oil, (12.0 g, 93%).

Workup

  1. customremoved from the ice bat h
  2. temperatureto warm to room temperature
  3. stirringstirred for 15 hours
  4. additionThe reaction mixture was diluted with dichloromethane
  5. washwashed with water, saturated sodium bicarbonate, and brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-2ea9144fece349eea69f4b5959898184
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

Loading…