Triphenylphosphine → [S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane

HRID 1109437Notes

Reaction equation

HRID 1109437 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 642409(1R)-3-chloro-1-phenylpropan-1-olHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 10045720[S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propaneYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound [S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane (Compound 12) was prepared in the same manner as Compound 2 in Example 1 but using [R]-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 1.58 g (69%) of Compound 12 as a thick pale yellow liquid: [α]25D +14.97 (c 10.73, CHCl3); 1H NMR (CDCl3, 250 MHz) δ 7.42-7.20 (m, 7H), 6.39 (d, J=8.8 Hz, 1H), 5.34 (dd, J=4.6, 8.8 Hz, 1H), 3.83-3.73 (m, 1H), 3.65-3.55 (m, 1H), 2.55-2.40 (m, 1H), 2.29-2.13 (m, 1H), 2.25 (s, 3H), FTIR (neat) 3050, 3015, 2950, 2900, 1600, 1480 (s), 1460, 1395, 1350, 1300, 1250(s), 1200, 1135 cm-1. Anal C17H20INO; C, H.

Workup

  1. customThe compound [S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane (Compound 12) was prepared in the same manner as Compound 2 in Example 1
  2. customat room temperature
  3. customfor 15 hours
  4. customWorkup and purification

Sources & evidence

ORD record
ord-267f39d6042d401d9785c50d0fe0dee1
Source dataset
uspto-grants-1994_06
Patent number
US05320825

Reaction notes

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