Hydrochloric Acid → HCID 178444219, compound

HRID 863731Notes

Reaction equation

HRID 863731 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][Si:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(OC(C)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[AlH4-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:9][CH2:10][Si@H:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28112Lithium aluminum hydrideHCID 19419993HCID 19419993, compound

Product 1

HCID 178444219HCID 178444219, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Subsequently, the reaction mixture was concentrated, to which 200 ml of hexane was added thereby permitting secondarily produced triethylamine hydrochloride to be precipitated and separated by filtration. The resultant filtrate was concentrated to obtain 28.2 g of 4-(p-fluorophenyl)-1-n-heptyl-1-isopropoxy-1-silacyclohexane. This silacyclohexane product was dissolved in 100 ml of THF and was added to 100 ml of a THF solution of 10.9 g of lithium aluminohydride, followed by agitation under reflux for 2 hours. The cis-trans isomer mixture was subjected to quantitative gas-chromatographic analysis in the same manner as set out in Example 1, revealing that a ratio of the cis isomer (retention time: 5.65 minutes) and the trans isomer (retention time: 5.71 minutes) was 15.85. The reaction mixture was poured into 200 ml of 5% hydrochloric acid and extracted with ethyl acetate. The extract was subjected to ordinary procedures of washing with brine, drying and concentration, followed by purification through silica gel chromatography to obtain 19.0 g of the intended product (yield: 72.6%). The result of IR and 13C-NMR analysis of the product are shown below.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate
  3. washof washing with brine
  4. customdrying
  5. concentrationconcentration
  6. customfollowed by purification through silica gel chromatography

Sources & evidence

ORD record
ord-97f14f91a6d64752b884fb765dc3e67d
Source dataset
uspto-grants-1996_10
Patent number
US05560866

Reaction notes

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