Triphenylphosphine → HCID 11165053, compound

HRID 1859054Notes

Reaction equation

HRID 1859054 reaction equation
[CH2:1]([N:8]1[CH2:12][C@:11]2([CH2:19][OH:20])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25](O)=[CH:24][C:23]=2[O:22]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@:11]2([CH2:19][O:20][C:26]3[CH:25]=[CH:24][C:23]4[O:22][CH2:21][O:29][C:28]=4[CH:27]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 68289SesamolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11414429HCID 11414429, compound

Product 1

HCID 11165053HCID 11165053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a three-necked flask, 3.5 g of the compound obtained in Step D, 2 g of 3,4-methylenedioxyphenol and 3.8 g of triphenylphosphine are mixed in 40 ml of tetrahydrofuran. The mixture is cooled to 0° C. and 2.4 ml of diethyl azodicarboxylate are added dropwise over a period of 20 minutes. After reacting for 4 days at ambient temperature, the reaction mixture is concentrated under reduced pressure. Chromatography on silica gel (CH2Cl2 /AcOEt: 95/5) allows 4.4 g of expected product to be isolated.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. customto be isolated

Sources & evidence

ORD record
ord-5f4acde57c4e401987beac6ac663e7b4
Source dataset
uspto-grants-2000_11
Patent number
US06153640

Reaction notes

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