Triphenylphosphine → HCID 10023063, compound

HRID 1109436Notes

Reaction equation

HRID 1109436 reaction equation
[Cl:1][CH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[I:12][C:13]1[CH:18]=[CH:17][C:16](O)=[C:15]([CH3:20])[CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O>C1COCC1>[Cl:1][CH2:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[O:5][C:16]1[CH:17]=[CH:18][C:13]([I:12])=[CH:14][C:15]=1[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1437134-Iodo-2-methylphenolHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanolHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 10023063HCID 10023063, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound [R]-(+)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane (Compound 5) was prepared in the same manner as for the preparation of Compound 2 in Example 1, but using [S]-3-chloro-1-phenylpropanol (1.0 g, 5.88 mmol), 4-iodo-2-methylphenol (1.38 g, 5.88 mmol), triphenylphosphine (1.54 g, 5.88 mmol), and ethyl azodicarboxylate (0.93 mL, 1.04 g, 5.88 mmol) in THF (15 mL) at room temperature for 15 hours. Workup and purification gave 1.60 g (70%) of Compound 5 as a thick pale yellow liquid: [απ25D +14.02 (c 7.7, CHCL3); 1H NMR (CDCl3, 250 MHz) δ 7.41-7.20 (m, 7H), 6.39 (d, J=8.8 Hz, 1H), 5.34 (dd, J=4.4, 8.8 Hz, 1H), 3.81-3 72 (m, 1H), 3.63-3.55 (m, 1H), 2.55-2.41 (m, 1H), 2.31-2.16 (m, 1H), 2.7 (s, 3H); FTIR (neat) 3080, 3020, 2970, 2915, 1585, 1485(s), 1450, 1390, 1360, 1290, 1245(s), 1180, 1130 cm-1. Anal. C17H20INO: C,H.

Workup

  1. customat room temperature
  2. customfor 15 hours
  3. customWorkup and purification

Sources & evidence

ORD record
ord-30ed96d438954171bb6cc4bfbfb0f9f9
Source dataset
uspto-grants-1994_06
Patent number
US05320825

Reaction notes

Loading…