Triethylamine → Methanesulfonic acid 3-benzyloxy-2,2-difluoropropyl ester

HRID 2279883Notes

Reaction equation

HRID 2279883 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([F:14])([F:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C:10]([F:13])([F:14])[CH2:11][O:12][S:16]([CH3:15])(=[O:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 584638693-(Benzyloxy)-2,2-difluoropropan-1-OL2×

Product 1

HCID 86697820Methanesulfonic acid 3-benzyloxy-2,2-difluoropropyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-benzyloxy-2,2-difluoropropan-1-ol (Compound 59H, 202 mg, 1 mmol) and methanesulfonyl chloride in DCM (3 mL) was cooled to 0° C. and treated with Et3N (0.28 mL, 2 mmol). The reaction mixture was allowed to warm at RT. After 12 h, the reaction mixture was diluted with DCM (5 mL) and washed with aq. K2CO3 (4×5 mL). The organic layer was dried over Na2SO4, filtered and concentrated to give 220 mg (82%) of the title compound as yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.37-7.33 (m, 5H), 4.62 (s, 2H), 4.47 (t, J=12.4 Hz, 2H), 3.74 (t, J=12.4 Hz, 2H), 3.05 (s, 3H).

Workup

  1. washwashed with aq. K2CO3 (4×5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16d2c48c314645a58532b4fc43eb499c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…