Hydrochloric Acid → HCID 178447765, compound

HRID 863730Notes

Reaction equation

HRID 863730 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH:15]3[CH2:20][CH2:19][Si:18]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(OCC)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[AlH4-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:14][CH2:13][C@H:12]([C@H:15]3[CH2:20][CH2:19][Si@H:18]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28112Lithium aluminum hydrideHCID 178447717HCID 178447717, compound

Product 1

HCID 178447765HCID 178447765, compoundYield 80.2%

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 urea hydrochloride to be precipitated and separated. The residual solution was concentrated to obtain 33.8 g of 4-(trans-4-(3,4-difluorophenyl)cyclohexyl)-1-n-pentyl-1-ethoxy-1-silacyclohexane. This silacyclohexane product was dissolved in 100 ml of THF and was added to 100 ml of a THF solution of 10.0 g of lithium aluminohydride, followed by agitation under reflux for 1 hour. 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: 9.56 minutes) and the trans isomer (retention time: 9.66 minutes) was 11:89. 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 25.2 g of the intended product (yield: 80.2%). This product exhibited nematic liquid crystal properties at a temperature between 14.3° and 71.6° C. and was found to be very useful as a liquid crystal substance. The results of IR analysis of the product are shown below.

Workup

  1. temperatureunder reflux for 1 hour
  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-fbe23c7a009348f88b344a269cd145e5
Source dataset
uspto-grants-1996_10
Patent number
US05560866

Reaction notes

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