Triphenylphosphine → HCID 19979960, compound

HRID 1461501Notes

Reaction equation

HRID 1461501 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[OH:13][C:14]1[CH:37]=[CH:36][C:17]([C:18]([O:20][CH:21]2[CH2:26][CH2:25][C:24]([C:34]#[N:35])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22]2)=[O:19])=[CH:16][CH:15]=1.C(C1(CCCCCCC)CCC(O)CC1)#N.C(OC1C=CC(C(O)=O)=CC=1)C1C=CC=CC=1.[C:71]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])(=[O:75])[CH:72]([CH3:74])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:34]([C:24]1([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:23][CH2:22][CH:21]([O:20][C:18]([C:17]2[CH:36]=[CH:37][C:14]([O:13][CH:72]([CH3:74])[C:71]([O:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH3:82])=[O:75])=[CH:15][CH:16]=2)=[O:19])[CH2:26][CH2:25]1)#[N:35]

Participants

8

Reactant 6

HCID 11776TriphenylphosphineHCID 738804-(Benzyloxy)benzoic acidHCID 519757Hexyl 2-hydroxypropanoateHCID 5462977Diethyl azodicarboxylateHCID 19979843HCID 19979843, compoundHCID 19979915HCID 19979915, compound

Product 1

HCID 19979960HCID 19979960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.5 g of diethylazodicarboxylate in tetrahydrofuran is added to a mixture of 20.6 g of 4-cyano-4-heptylcyclohexyl p-hydroxybenzoate (obtainable by esterification of 4-cyano-4-heptylcyclohexanol with p-benzyloxybenzoic acid and cleavage of the benzyl group by catalytic hydrogenation), 11.5 g of optically active hexyl lactate and 15.7 g of triphenylphosphine in 150 ml of tetrahydrofuran, stirring is carried out for one hour at 50° and the solvent is removed after 12 hours. The residue is dissolved in 100 ml of hot toluene, cooled down, filtered and the filtrate purified as usual by chromatography and crystallization. Optically active hexyl p-(4-cyano-4-heptylcyclohexyloxycarbonyl)phenoxypropionate is obtained.

Workup

  1. customthe solvent is removed after 12 hours
  2. dissolutionThe residue is dissolved in 100 ml of hot toluene
  3. temperaturecooled down
  4. filtrationfiltered
  5. customthe filtrate purified as
  6. customusual by chromatography and crystallization

Sources & evidence

ORD record
ord-3184735d6ead47738da1420aa5353d4a
Source dataset
uspto-grants-1991_12
Patent number
US05075032

Reaction notes

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