4-Toluenesulfonyl chloride → HCID 59288334, compound

HRID 2420638Notes

Reaction equation

HRID 2420638 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]([CH2:15][OH:16])[CH2:13]O)[O:8][CH2:7][CH:6]([CH2:17][CH2:18][CH3:19])[CH2:5]2.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12]1[CH2:15][O:16][CH2:13]1)[O:8][CH2:7][CH:6]([CH2:17][CH2:18][CH3:19])[CH2:5]2

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 59288344HCID 59288344, compoundHCID 178418339Butyllithium2×

Product 1

HCID 59288334HCID 59288334, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

3.80 g (13.7 mmol) of 2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol are dissolved in 70 ml of THF, and 8.7 ml (13.7 mmol) of a 15 percent solution of n-butyllithium in hexane are added at 0° C. After 30 min, 2.7 g (14.2 mmol) of p-toluenesulfonyl chloride in 30 ml of THF are added, and the mixture is stirred at RT for 1 h and re-cooled to 0° C. After addition of a further 8.7 ml (13.7 mmol) of a 15% solution of n-butyllithium in hexane, the cooling is removed, and the batch is heated under reflux for 4 h. The batch is subsequently diluted with MTB ether and washed with water. The org. phase is dried over sodium sulfate and evaporated, and the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2). The product fractions (Rf=0.5) are evaporated, and the product is used without further purification.

Workup

  1. temperaturere-cooled to 0° C
  2. customthe cooling is removed
  3. temperaturethe batch is heated
  4. temperatureunder reflux for 4 h
  5. additionThe batch is subsequently diluted with MTB ether
  6. washwashed with water
  7. dry with materialphase is dried over sodium sulfate
  8. customevaporated
  9. customthe crude product is purified by chromatography on silica gel with heptane/ethyl acetate (3:2)
  10. customThe product fractions (Rf=0.5) are evaporated
  11. customthe product is used without further purification

Sources & evidence

ORD record
ord-4dd5ac3a52fc404d8611572a00b81c55
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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