Ethyl Lactate → HCID 19979930, compound

HRID 1461500Notes

Reaction equation

HRID 1461500 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:31][CH2:30][C:29]([C:40]#[N:41])([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.[C:42]([O:47][CH2:48][CH3:49])(=[O:46])[CH:43]([CH3:45])O>O1CCCC1>[C:40]([C:29]1([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:28][CH2:27][CH:26]([C:23]2[CH:24]=[CH:25][C:20]([C:17]3[CH:16]=[CH:15][C:14]([O:13][CH:43]([CH3:45])[C:42]([O:47][CH2:48][CH3:49])=[O:46])=[CH:19][CH:18]=3)=[CH:21][CH:22]=2)[CH2:31][CH2:30]1)#[N:41]

Participants

5

Reactant 3

HCID 7344Ethyl LactateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19809977HCID 19809977, compound

Product 1

HCID 19979930HCID 19979930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.6 g of diethyl azodicarboxylate dissolved in tetrahydrofuran is added to a mixture of 19.4 g of 4-(4'-hydroxybiphenyl-4-yl)-1-cyano-1-octylcyclohexane, 6.5 g of ethyl lactate and 13.1 g of triphenylphosphene in 300 ml of tetrahydrofuran, stirring is carried out for one hour at 50°, the mixture is allowed to stand overnight, the solvent is removed and the residue is taken up in 100 ml of hot toluene. After the toluene solution has been cooled to 0°, it is filtered and the product is isolated from the filtrate as usual by chromatography. Optically active ethyl 2-[4'-(4-cyano-4-octylcyclohexyl)biphenyl-4-yloxy]propionate is obtained.

Workup

  1. waitto stand overnight
  2. customthe solvent is removed
  3. temperatureAfter the toluene solution has been cooled to 0°
  4. filtrationit is filtered
  5. customthe product is isolated from the filtrate as usual by chromatography

Sources & evidence

ORD record
ord-b36cf44ee0204a81994cf33e1d63986f
Source dataset
uspto-grants-1991_12
Patent number
US05075032

Reaction notes

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