4-Toluenesulfonyl chloride → (R)-Toluene-4-sulfonic acid 3-benzyloxymethoxy-2-methyl-propyl ester

HRID 493060Notes

Reaction equation

HRID 493060 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@H:12]([CH3:15])[CH2:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:23](Cl)([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:15])[CH2:13][O:14][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11805955(2R)-3-Benzyloxymethoxy-2-methyl-propan-1-ol

Product 1

HCID 57680470(R)-Toluene-4-sulfonic acid 3-benzyloxymethoxy-2-methyl-propyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of diol 3 (29.2 mmol, 6.13 g), DMAP (0.82 mmol, 100 mg) and triethylamine (116.7 mmol, 16.2 mL, 11.8 g) in anhydrous CH2Cl2 (60 mL) was added tosyl chloride (37.9 mmol, 7.23 g) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued overnight. The mixture was then diluted with CH2Cl2 (100 mL) and was then washed with a saturated aqueous solution of NaHCO3, dried over Na2SO4, and concentrated under reduced pressure. The residue was chromatographed on a silica gel using hexane/EtOAc (7:3) as an eluent to give the oily tosylate 4 (10.2 g, 97%).

Workup

  1. washwas then washed with a saturated aqueous solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-90137c7ce6f347fcb8691c1e954ae976
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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