Isopropyl iodide → HCID 54272250, compound

HRID 1395605Notes

Reaction equation

HRID 1395605 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7]OC[CH2:4]1.[C:8]1([CH:14]=[CH:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(I)(C)C>CN(P(N(C)C)(N(C)C)=O)C>[CH:3]([CH:16]([CH:15]=[CH:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:7])[CH3:4]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 37030883-Butenoic acid, 4-phenyl-, ethyl ester

Product 1

HCID 54272250HCID 54272250, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To sodium hydride (2.84 g, 57% in oil, washed with pentane), 110 ml dry THF and 20 ml HMPT, cooled to 0° and under nitrogen, is added 12.7 g ethyl 4-phenyl-3-butenoate slowly with stirring. Then 6.5 ml of isopropyliodide is added and the reaction mixture is stirred for about 60 hrs. The reaction is worked up by extracting into water/ether mixture. The aqueous phase is extracted with ether. The organic phases are combined, washed with brine, dried over calcium sulfate and rotoevaporated to give ethyl 2-isopropyl-4-phenyl-3-butenoate, which is hydrolyzed (potassium hydroxide, water-methanol) to the acid, 2-isopropyl-4-phenyl-3-butenoic acid. The acid is reacted with m-phenoxybenzyl alcohol following the procedure of Example 4 to yield m-phenoxybenzyl ester of 2-isopropyl-4-phenyl-3-butenoic acid. NMR (CDCl3) δ0.91 [d, 3, J=Hz, --CH(CH3)2 ], 0.94 [d, 3, J=Hz, --CH(CH3)2 ], 5.13 (s, 2, benzyl), and 6.0-6.5 ppm (complex, 2, vinyl). IR (CCl4) 1745 cm-1 (C=O).

Workup

  1. stirringthe reaction mixture is stirred for about 60 hrs
  2. extractionby extracting into water/ether mixture
  3. extractionThe aqueous phase is extracted with ether
  4. washwashed with brine
  5. dry with materialdried over calcium sulfate

Sources & evidence

ORD record
ord-27f670f59cfe4b2388527133b8599b99
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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