Pyridine → HCID 86612733, compound

HRID 1821545Notes

Reaction equation

HRID 1821545 reaction equation
[CH2:1]([O:8][C@@H:9]([CH3:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([OH:19])[CH2:17][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.C(OCC)C>CCCCCC.C(OCC)(=O)C>[CH2:1]([O:8][C@@H:9]([CH3:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([OH:19])[CH2:17][O:18][S:33]([C:30]1[CH:31]=[CH:32][C:27]([CH3:37])=[CH:28][CH:29]=1)(=[O:35])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 69049493HCID 69049493, compound

Product 1

HCID 86612733HCID 86612733, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice cold solution of 4.6 g (16.4 mmol) (2R,9S)-9-benzyloxydecane-1,2-diol in 50 ml abs. pyridine was slowly added a solution of 2.9 g (15 mmol) p-toluene sulfonyl chloride in 20 ml abs. pyridine. Stirring was continued for 5 h at 0° C. and 12 h at 4° C. Subsequently, 150 ml ice water (brought to pH 5 with 0.1% hydrochloric acid) were added and 60 ml diethyl ether. Subsequently, the aqueous layer was extracted four times with 120 ml diethyl ether. The combined organic layers were washed three times with 100 ml of an aqueous, saturated solution of copper-II-sulphate and two times with 100 ml brine. The organic layer was dried over magnesium sulphate and concentrated in vacuo. Flash chromatography (10% ethyl acetate in hexane) furnished 4.6 g (10.5 mmol, 64%) (2R,9S)-9-benzyloxy-1 (p-tolylsulfonyloxy)decane-2-ol.

Workup

  1. extractionSubsequently, the aqueous layer was extracted four times with 120 ml diethyl ether
  2. washThe combined organic layers were washed three times with 100 ml of an aqueous, saturated solution of copper-II-sulphate and two times with 100 ml brine
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31c4ef2b6b3a4455afb694dd96864d52
Source dataset
uspto-grants-2009_10
Patent number
US07608254B2

Reaction notes

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