Hydrochloric Acid → HCID 53809068, compound

HRID 1732267Notes

Reaction equation

HRID 1732267 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 21/2 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 aqueous 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, CH3CH<), 1.05 [s, (CH3)3 ], 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 aqueous 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-7887e638ccef44e182c1349b6cea5657
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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