4-Toluenesulfonyl chloride → HCID 68923680, compound

HRID 1686179Notes

Reaction equation

HRID 1686179 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[CH:7](O)[CH:6]([CH2:13][CH:14]([CH2:20][OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5]2.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.FC1C=C2C(=CC=1F)C1OCC(CCCCC)CC1C2>ClCCl.N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C@@H:7]1[O:21][CH2:20][C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:13][C@H:6]1[CH2:5]2

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 57702262HCID 57702262, compoundHCID 57702294HCID 57702294, compound

Product 1

HCID 68923680HCID 68923680, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

6.0 g (21.4 mmol) of 5,6-difluoro-2-(2-hydroxymethylheptyl)indan-1-ol are dissolved in 70 ml of dichloromethane and 10 ml of pyridine, and 9.5 g (50 mmol) of p-toluenesulfonyl chloride are added with ice-cooling. The cooling is removed, and the batch is left to stir at room temp. overnight. After addition of 100 ml of dichloromethane, the solution is washed three times with 2 N hydrochloric acid and once each with water and copper sulfate solution and dried over sodium sulfate. The solvent is removed in vacuo, giving an isomer mixture of 7,8-difluoro-3-pentyl-2,3,4,4a,5,9b-hexahydroindeno[1,2-b]pyran, which is separated by chromatography on silica gel (eluent heptane/toluene 5:1), giving the racemate of (3R*,4aS*,9bR*)-7,8-difluoro-2,3,4,4a,5,9b-hexahydro-3-pentylindeno[1,2-b]pyran and the enantiomer thereof as a colourless solid; Δ∈=13.4; Δn=0.1021.

Workup

  1. temperaturecooling
  2. customThe cooling is removed
  3. waitthe batch is left
  4. additionAfter addition of 100 ml of dichloromethane
  5. washthe solution is washed three times with 2 N hydrochloric acid
  6. dry with materialonce each with water and copper sulfate solution and dried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. customgiving
  9. customis separated by chromatography on silica gel (eluent heptane/toluene 5:1)

Sources & evidence

ORD record
ord-e28dc1d4ecc34e5bbebc72bda6bcb22d
Source dataset
uspto-grants-2012_04
Patent number
US08148551B2

Reaction notes

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