Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86742992, compound

HRID 1761767Notes

Reaction equation

HRID 1761767 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][CH:7]([CH2:11][CH2:12]/[C:13](/[CH3:28])=[CH:14]/[CH2:15][CH2:16]/[C:17](/[CH3:27])=[CH:18]\[CH2:19][O:20]C1CCCCO1)[C:8]([CH3:10])=[CH2:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C)C>[C:1]([Si:5]([CH3:29])([CH3:30])[O:6][CH:7]([C:8]([CH3:10])=[CH2:9])[CH2:11][CH2:12]/[C:13](/[CH3:28])=[CH:14]/[CH2:15][CH2:16]/[C:17](/[CH3:27])=[CH:18]\[CH2:19][OH:20])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 70394004HCID 70394004, compound

Product 1

HCID 86742992HCID 86742992, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The product, containing (6E,10Z)-3-(tert.-butyldimethylsilyloxy)-2,6,10-trimethyl-12-[(tetrahydro-2H-pyran-2-yl)oxy]-1,6,10-dodecatriene, is dissolved in 50 ml of isopropanol and treated with 350 mg of pyridinium p-toluenesulfonate. The reaction solution is stirred at room temperature for 6 hours under argon. After aqueous working-up the organic phase is dried and freed from the solvents. The residue is chromatographed on silica gel with ether-hexane 2:1. There is obtained (2Z,6E)-10-(tert.butyldimethylsilyloxy)-3,7,11-trimethyl-2,6,11-dodecatrien-1-ol which exhibits the following absorption bands in the IR spectrum: 3339 cm-1, 3071 cm-1, 1666 cm-1, 1651 cm-1, 1448 cm-1, 1251 cm-1, 1078 cm-1, 1022 cm-1, 1004 cm-1.

Workup

  1. customAfter aqueous working-up the organic phase is dried
  2. customThe residue is chromatographed on silica gel with ether-hexane 2:1

Sources & evidence

ORD record
ord-c851a0cc9dfd4346acb8afabcd4b64b3
Source dataset
uspto-grants-1989_05
Patent number
US04827004

Reaction notes

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