Hydrochloric Acid → HCID 178447771, compound

HRID 863729Notes

Reaction equation

HRID 863729 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([CH:17]3[CH2:22][CH2:21][Si:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(OC)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[F:8].[AlH4-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C@H:11]2[CH2:12][CH2:13][C@H:14]([C@H:17]3[CH2:22][CH2:21][Si@H:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28112Lithium aluminum hydrideHCID 178447718HCID 178447718, compound

Product 1

HCID 178447771HCID 178447771, compoundYield 86.3%

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, followed by removal by filtration. The resultant filtrate was concentrated to obtain 34.6 g of 4-(trans-4-(2-(3,4-difluorophenyl)ethyl)cyclohexyl)-1-n-pentyl-1-methoxy-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 hereinabove, revealing that a ratio of the cis isomer (retention time: 11.35 minutes) and the trans isomer (retention time: 11.61 minutes) was 12:88. 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 28.9 g of an intended product (yield: 86.3%). This product exhibited nematic liquid crystal properties at a temperature between 7.6° and 69.7° 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-265b7be392b743d09d87f1ab52daae42
Source dataset
uspto-grants-1996_10
Patent number
US05560866

Reaction notes

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