Hydrochloric Acid → {4-[2-(4-Dimethylamino-but-1-enyl)-benzyloxy]-3-iodo-phenyl}-acetic acid methyl ester

HRID 1433312Notes

Reaction equation

HRID 1433312 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[I-].[CH3:12][N:13]([CH3:36])[CH2:14][CH2:15][CH2:16][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:37][O:38][C:39](=[O:58])[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH:55]=O)=[C:43]([I:57])[CH:42]=1.Cl>C1(C)C=CC=CC=1>[CH3:37][O:38][C:39](=[O:58])[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[CH:55]=[CH:16][CH2:15][CH2:14][N:13]([CH3:36])[CH3:12])=[C:43]([I:57])[CH:42]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11690056[4-(2-Formylbenzyloxy)-3-iodophenyl]acetic Acid Methyl EsterHCID 60201283(3-Dimethylamino-propyl)-triphenyl-phosphonium iodide

Product 1

HCID 68911643{4-[2-(4-Dimethylamino-but-1-enyl)-benzyloxy]-3-iodo-phenyl}-acetic acid methyl esterYield 177.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Potassium bis(trimethylsilyl)amide (KHMDS) (0.5M in toluene, 102.5 ml, 51 mmol) was slowly added to a dispersion of (3-Dimethylamino-propyl)-triphenyl-phosphonium iodide (24.3 g, 51 mmol) in anhydrous toluene (60 ml) at room temperature and in an inert atmosphere. The mixture was stirred at this temperature for 1 hour and then [4-(2-Formyl-benzyloxy)-3-iodo-phenyl]-acetic acid methyl ester (5 g, 12 mmol) in anhydrous toluene was added and was stirred at this temperature for 2 h 30 min. Hydrochloric acid 2N was added to the mixture and organic layers were washed with HCl 2N. Watery layers were washed with toluene and were alkalized with K2CO3. The aqueous layers were extracted with ethyl acetate, were filtered, dried and concentrated to dryness to obtain 10.2 g (73%) {4-[2-(4-Dimethylamino-but-1-enyl)-benzyloxy]-3-iodo-phenyl}-acetic acid methyl ester (72:28 Z/E), that was used, without having been purified in the following step.

Workup

  1. stirringwas stirred at this temperature for 2 h 30 min
  2. washwere washed with HCl 2N
  3. washWatery layers were washed with toluene
  4. extractionThe aqueous layers were extracted with ethyl acetate
  5. filtrationwere filtered
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f516026512c64bfc94867dc0d9962aae
Source dataset
uspto-grants-2009_11
Patent number
US07612219B2

Reaction notes

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