p-Toluenesulfonic acid → (2R,6S)-2-Tetrahydropyranyloxy-6-methyloctyl p-toluenesulfonate

HRID 2289370Notes

Reaction equation

HRID 2289370 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@H:12]([OH:20])[CH2:13][CH2:14][CH2:15][C@@H:16]([CH3:19])[CH2:17][CH3:18])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)C>[C:1]1([CH3:21])[CH:2]=[CH:3][C:4]([S:7]([O:10][CH2:11][C@H:12]([O:20][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][O:22]2)[CH2:13][CH2:14][CH2:15][C@@H:16]([CH3:19])[CH2:17][CH3:18])(=[O:8])=[O:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 57007664HCID 57007664, compound

Product 1

HCID 57087675(2R,6S)-2-Tetrahydropyranyloxy-6-methyloctyl p-toluenesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.85 g of (2R,6S)-2-hydroxy-6-methyloctyl p-toluenesulfonate obtained in Step 5, 0.8 g of 3,4-dihydro-2H-pyran, 28 ml of diethyl ether, and 0.28 g of p-toluenesulfonic acid was allowed to react in a flask for 6 hours. The resulting solution was poured into 100 ml of a 1% sodium hydrogencarbonate aqueous solution, extracted with diethyl ether, washed with water, and concentrated to obtain 3.58 g of a crude product, which was then purified by HPLC to obtain 2.13 g (99%) of the titled compound.

Workup

  1. customto react in a flask for 6 hours
  2. extractionextracted with diethyl ether
  3. washwashed with water
  4. concentrationconcentrated
  5. customto obtain 3.58 g of a crude product, which
  6. customwas then purified by HPLC

Sources & evidence

ORD record
ord-68d95618c2c84d44b33d22f3dd2d8ead
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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