p-Toluenesulfonic acid → HCID 70415731, compound

HRID 622616Notes

Reaction equation

HRID 622616 reaction equation
[PH3]=[O:2].[OH:3][C:4]([CH3:22])([CH3:21])[CH2:5][CH2:6][P:7](=[O:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:23]1(C)C=[CH:27][C:26](S(O)(=O)=O)=[CH:25][CH:24]=1>C1C=CC=CC=1>[O:2]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:3][C:4]([CH3:22])([CH3:21])[CH2:5][CH2:6][P:7](=[O:20])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21291216HCID 21291216, compoundHCID 178527022HCID 178527022, compound

Product 1

HCID 70415731HCID 70415731, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The phosphine oxide from (f) above (1.4 g) was dissolved in dihydripyran (20 ml) and benzene (5 ml). p-Toluenesulphonic acid (10 mg) was added. After 20 hr, the mixture was concentrated, added to CH2Cl2 and washed with 5% aqueous NaHCO3 /brine and dried. Evaporation of the solvent gave the crude product (1.8 g) essentially quantitatively as a solid. Recrystallised from acetone. m.p. 146°-148° C.; 1Hnmr δ 8.0-7.3 (m, 10 H, aryl), 4.67 (m, W=6 Hz, THP, C-2'H), 3.67 (m, W=36 Hz, THP, C-6'H2), 1.23 (s, 6H); IR νmax 2950 (m), 1440 (m), 118C (s), cm-1 ; (analysis found: % C, 70.80; H, 7.73; P, 8.54; C22H29O3P requires % C, 70.96; H, 7.85; P, 8.32.

Workup

  1. concentrationthe mixture was concentrated
  2. additionadded to CH2Cl2
  3. washwashed with 5% aqueous NaHCO3 /brine
  4. customdried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-641e3e0d32f7400488d3f4f8219356d7
Source dataset
uspto-grants-1988_09
Patent number
US04772433

Reaction notes

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