Hydrochloric Acid → HCID 53809068, compound

HRID 1448936Notes

Reaction equation

HRID 1448936 reaction equation
[O:1]([CH2:19][CH:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24]1(OCC[O:26]1)[CH3:25])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[O:1]([CH2:19][CH:20]([CH3:30])[CH2:21][CH2:22][CH2:23][C:24](=[O:26])[CH3:25])[Si:2]([C:15]([CH3:16])([CH3:17])[CH3:18])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20284854HCID 20284854, compound

Product 1

HCID 53809068HCID 53809068, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-t-Butyldiphenylsiloxy-6,6-ethylenedioxy-2-methyl-heptane (75.35 g) in acetone (2 l) is treated with 10 % hydrochloric acid (75 ml) and the solution is allowed to stir at room temperature for two and one half hours. The reaction mixture is neutralized with a saturated sodium bicarbonate solution (150 ml), the salt is removed by filtration and the solvent is removed in vacuo. The resulting residue is partitioned between ether and water, the aqueoous phase is extracted with ether, and the combined ether extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give the crude product which is purified via silica gel chromatography (5% (EtOAc/hexane) to give 1-t-butyldiphenylsiloxy-2-methyl-6-oxo-heptane (61.95 g, 92%); ir (neat 5.85 μ (C=O; nmr (CDCl3,δ), 0.92 (d, 3H, ##STR59## 1.05 (CH3)3C], 2.07 (s, 3H, CH3C=O), 3.45 (d, 2H, CHCH2O), 7.2-7.8 (m, 10H, 2φ).

Workup

  1. customthe salt is removed by filtration
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is partitioned between ether and water
  4. extractionthe aqueoous phase is extracted with ether
  5. washthe combined ether extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is removed in vacuo
  8. customto give the crude product which
  9. customis purified via silica gel chromatography (5% (EtOAc/hexane)

Sources & evidence

ORD record
ord-e4b1f5a21afe461da68334fe8282cdcd
Source dataset
uspto-grants-1980_02
Patent number
US04188328

Reaction notes

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