Methanesulfonyl chloride → (2S)-1-(4-cyanophenoxy)-3-methane-sulfonyloxypropan-2-ol

HRID 466222Notes

Reaction equation

HRID 466222 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][CH:4]=1)#[N:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C@H:9]([OH:12])[CH2:10][O:11][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12222186(2R)-3-(4-cyanophenoxy)propane-1,2-diol

Product 1

HCID 15066864(2S)-1-(4-cyanophenoxy)-3-methane-sulfonyloxypropan-2-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

57.2 g of (2R)-3-(4 cyanophenoxy)propane-1,2-diol was dissolved in dry pyridine, (300 ml) and treated dropwise with methanesulfonyl chloride, (20.7 ml), at -10° C. The reaction mixture was kept at 5° C. overnight, evaporated at reduced pressure and poured on ice and 2 M hydrochloric acid. The solid precipitate was recrystallized three times from methanol to yield 12.3 g of the title compound, m.p. 119°-121° C., [α]D20 +9.7° (c 1.0, CH3OH).

Workup

  1. customevaporated at reduced pressure
  2. additionpoured on ice and 2 M hydrochloric acid
  3. customThe solid precipitate was recrystallized three times from methanol

Sources & evidence

ORD record
ord-1f2068e8415c42a5ac0d8a34e1ff74c8
Source dataset
uspto-grants-1992_10
Patent number
US05155133

Reaction notes

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