Ammonium Chloride → Methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate

HRID 1920579Notes

Reaction equation

HRID 1920579 reaction equation
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([O:36][C:37](=[O:59])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44]([CH:57]=O)[CH2:45][CH2:46][C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)[CH2:41][CH2:40]1)[CH3:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:34]([O:36][C:37](=[O:59])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44](/[CH:57]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][CH2:46][C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)[CH2:41][CH2:40]1)[CH3:35]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57965765Methyl 4-{5-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-3-formylpentyl}benzoateHCID 178418339Butyllithium

Product 1

HCID 57965770Methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

At 0° C., 0.6 ml (1.5 mmol) of a 2.5 M solution of n-butyllithium in hexane is slowly added to a solution of 359 mg (0.799 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 5 ml of anhydrous THF, and the mixture is stirred for 45 min. At this temperature, 192 mg (0.53 mmol) of methyl 4-{5-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-3-formylpentyl}benzoate are then added slowly, and the mixture is stirred at 0° C. for 2 hours. After complete conversion, saturated ammonium chloride solution is added to the reaction solution, which is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 178.5 mg (74% of theory) of a colorless oil.

Workup

  1. stirringthe mixture is stirred at 0° C. for 2 hours
  2. concentrationis then concentrated to dryness
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-fbc0edfa9b324e3a85db8cde2ae34538
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

Loading…