p-Toluenesulfonic acid → HCID 57017871, compound

HRID 1197507Notes

Reaction equation

HRID 1197507 reaction equation
[CH3:1][C:2](=[CH:4][C@H:5]([OH:10])[C@H:6]([OH:9])[CH2:7][CH3:8])[CH3:3].[C:11]1(C)[CH:16]=CC(S(O)(=O)=O)=C[CH:12]=1.COC(OC)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:12][C:11]1([CH3:16])[O:10][C@@H:5]([CH2:4][CH:2]([CH3:3])[CH3:1])[C@@H:6]([CH:7]=[CH2:8])[O:9]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 57150098HCID 57150098, compound

Product 1

HCID 57017871HCID 57017871, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the crude alcohol resulting from Example 9A dissolved in dichloromethane was added p-toluenesulfonic acid (500 mg) and 2,2-dimethoxypropane. The reaction was stirred at ambient temperature for 24 hours and poured into saturated sodium bicarbonate solution. The organic phase was separated, dried over magnesium sulfate and concentrated by distillation to give the title compound. 1H NMR (CDCl3, 300 MHz) δ0.92 (d, J=6 Hz, 3H), 0.96 (d, J-6 Hz, 3H), 1.17 (ddd, J=4.5, 9.0, 15 Hz, 1H), 1.38 (s, 3H), 1.48 (s, 3H), 1.75 (m, 1H), 4.24 (ddd, J=3, 6, 9 Hz, 1H), 4.48 (m, 1H), 5.22 (ddd, J=1, 2, 9 Hz, 1H), 5.27 (ddd, J=1, 2, 17 Hz, 1H), 5.81 (ddd, J=7.5, 9, 17 Hz, 1H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by distillation

Sources & evidence

ORD record
ord-4a678e6badec4001973d23b2187249b8
Source dataset
uspto-grants-1994_01
Patent number
US05275950

Reaction notes

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