Diethyl Ether → HCID 20028720, compound

HRID 1722367Notes

Reaction equation

HRID 1722367 reaction equation
ClC1(Cl)C(=O)[CH2:8][CH:7]2[CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C.CC[O:27][CH2:28][CH3:29]>C(O)(=O)C.[Zn]>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:6]12[CH2:29][C:28](=[O:27])[CH2:8][CH:7]1[CH2:3][CH2:4][CH2:5]2

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 150530136,6-Dichloro-2-(5-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.3.0]octan-7-one2×

Product 1

HCID 20028720HCID 20028720, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

The starting material, 6,6-dichloro-2-(5-[(1,1-dimethylethyl)dimethylsiloxy]pent-1-yl)bicyclo[3.3.0]octan-7-one {1,1-dichloro-4-[5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]pentyl]hexahydro-2(1H)-pentalenone} (12.1 g, 0.30 moles) is dissolved in glacial acetic acid (85 ml) and the solution is stirred while zinc (25 g) is slowly added. The reaction is heated at 70° C. for 1 hour, after which time ether (100 ml) is added and the solution filtered. The filtrate is washed with brine and then neutralized with saturated sodium bicarbonate. The ether layer is separated and dried over anhydrous sodium sulfate. The solvent is removed under vacuum leaving a clear yellow oil. The crude product is chromatographed on silica gel and subsequently kugelrohred under vacuum leaving a clear, colorless oil (0.72 g, 3.4 mmoles).

Workup

  1. additionis slowly added
  2. filtrationthe solution filtered
  3. washThe filtrate is washed with brine
  4. customThe ether layer is separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed under vacuum
  7. customleaving a clear yellow oil
  8. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-07de6f9d07274b2d8da701a3827ee4ce
Source dataset
uspto-grants-1989_08
Patent number
US04855322

Reaction notes

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