Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (5S,7S)-5,7-bis-(tert-butyldiphenyl-silanyloxy)-non-8-en-2-yn-1-ol

HRID 1604846Notes

Reaction equation

HRID 1604846 reaction equation
[Si:1]([O:18][C@H:19]([CH2:31][C@H:32]([O:35][Si:36]([C:49]([CH3:52])([CH3:51])[CH3:50])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH:33]=[CH2:34])[CH2:20][C:21]#[C:22][CH2:23][O:24]C1CCCCO1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:14]([Si:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[O:18][C@H:19]([CH2:31][C@H:32]([O:35][Si:36]([C:49]([CH3:50])([CH3:51])[CH3:52])([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH:33]=[CH2:34])[CH2:20][C:21]#[C:22][CH2:23][OH:24])([CH3:15])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57039693(5S,7S)-2-[5,7-bis-(tert-butyl-diphenyl-silanyloxy)-non-8-en-2-ynyloxy]-tetrahydropyran

Product 1

HCID 57269476(5S,7S)-5,7-bis-(tert-butyldiphenyl-silanyloxy)-non-8-en-2-yn-1-olYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25.16 g (34.4 mmol) of (5S,7S)-2-[5,7-bis-(tert-butyl-diphenylsilanyloxy)-non-8-en-2-ynyloxy]-tetrahydro-pyran was deprotected by treatment at ambient temperature with 1.30 g (15 mol %) of pyridinium p-toluenesulfonate in 290 ml of abs. MeOH. The solution gradually became homogeneous. After 18 h the reaction mixture was quenched by pouring onto crushed ice/Na2CO3, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=82/18) yielded 19.17 g of (5S,7S)-5,7-bis-(tert-butyldiphenyl-silanyloxy)-non-8-en-2-yn-1-ol as yellowish crystals of mp. 114-116°.

Workup

  1. customAfter 18 h the reaction mixture was quenched
  2. additionby pouring
  3. customonto crushed ice/Na2CO3
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-da50bd0a86694ef3962074fb2ef2d85a
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Reaction notes

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