Sodium borohydride → HCID 178509566, compound

HRID 1872309Notes

Reaction equation

HRID 1872309 reaction equation
COC(/C=C/C1C=CC(C2C=CC(C3CCC(CCCOC(C(C)=C)=O)CC3)=CC=2)=CC=1)=O.[O:34]=[CH:35][CH2:36][CH2:37][C@H:38]1[CH2:43][CH2:42][C@H:41]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=3)=[CH:46][CH:45]=2)[CH2:40][CH2:39]1.[BH4-].[Na+]>CO.CCOCC>[OH:34][CH2:35][CH2:36][CH2:37][C@H:38]1[CH2:39][CH2:40][C@H:41]([C:44]2[CH:49]=[CH:48][C:47]([C:50]3[CH:51]=[CH:52][C:53]([C:56]#[N:57])=[CH:54][CH:55]=3)=[CH:46][CH:45]=2)[CH2:42][CH2:43]1

Participants

5

Reactant 3

HCID 4311764Sodium borohydride2×HCID 18329222HCID 18329222, compoundHCID 178509565HCID 178509565, compound

Product 1

HCID 178509566HCID 178509566, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent2×

Procedure

The polymerization of 3-[4-[4'-[(E)-2-methoxycarbonyl-vinyl]-biphenyl-4-yl]-cyclohexyl]-propyl trans-2-methyl-acrylate to poly [1-[3-[4-[4'-[(E)-2-methoxycarbonyl-vinyl]-biphenyl-4-yl]-cyclohexyl]-propoxycarbonyl]-1-methyl-ethylene] was effected analogously to Example 1. The polymer has the following phase succession (° C.): G 156 C 208 l The 3-[4-[4'-[(E)-2-methoxycarbonyl-vinyl]-biphenyl-4-yl]-cyclohexyl]-propyl trans-2-methyl-acrylate used as the starting material was prepared according to the following procedure: ##STR28## A solution of 12 g of trans-4'-[4-(3-oxo-propyl)-cyclohexyl]-biphenyl-4-carbonitrile (preparation: Mol. Cryst. Liq. Cryst. 1985, Vol. 131, 327) in 100 ml methanol/ether (9:1) was added dropwise at 0° C. within 5 minutes to a suspension of 1.39 g of sodium borohydride in 30 ml of methanol/ether (9:1). After 45 minutes a further 1 g of sodium borohydride was added. After a further hour the reaction was interrupted and the mixture was partitioned between methylene chloride and 1N hydrochloric acid. Thereupon, the organic phase was washed several times with water, dried over magnesium sulphate, filtered and evaporated. Crystallization from ethyl acetate/methylene chloride gave 11.5 g of trans-4'-[4-(3-hydroxy-propyl)-cyclohexyl]-biphenyl-4-carbonitrile as yellowish crystals. ##STR29##

Workup

  1. customwas prepared
  2. waitAfter a further hour the reaction was interrupted
  3. customthe mixture was partitioned between methylene chloride and 1N hydrochloric acid
  4. washThereupon, the organic phase was washed several times with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customCrystallization from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-fc38d0d9b8d74eeab08db688017bf4fa
Source dataset
uspto-grants-2000_08
Patent number
US06107427

Reaction notes

Loading…