Ammonium Chloride → HCID 59180513, compound

HRID 1913794Notes

Reaction equation

HRID 1913794 reaction equation
C([Li])CCC.[Br-].[F:7][C:8]1[CH:9]=[CH:10][C:11]([OH:34])=[C:12]([CH:33]=1)[CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:35]([CH:37]([CH2:49][CH2:50][C:51]1[CH:60]=[CH:59][C:54]([C:55]([O:57][CH3:58])=[O:56])=[CH:53][CH:52]=1)[CH2:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1)=O.[Cl-].[NH4+]>CCCCCC.C1COCC1.O.C(OCC)(=O)C>[F:7][C:8]1[CH:9]=[CH:10][C:11]([OH:34])=[C:12](/[CH:13]=[CH:35]/[CH:37]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=2)[CH2:49][CH2:50][C:51]2[CH:60]=[CH:59][C:54]([C:55]([O:57][CH3:58])=[O:56])=[CH:53][CH:52]=2)[CH:33]=1

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 59180526Dimethyl 4,4'-(2-formylbutane-1,4-diyl)dibenzoateHCID 86638793(5-Fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromideHCID 178418339Butyllithium

Product 1

HCID 59180513HCID 59180513, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

21.65 ml (54.12 mmol) of a 2.5 M solution of n-butyllithium in hexane are slowly added dropwise to a solution of 10.84 g (23.2 mmol) of (5-fluoro-2-hydroxybenzyl)(triphenyl)phosphonium bromide in 150 ml of THF at 0° C., and the mixture is stirred at this temperature for 45 min. Subsequently, at this temperature, 6.85 g (19.33 mmol) of dimethyl 4,4′-(2-formylbutane-1,4-diyl)dibenzoate in 100 ml of THF are slowly metered in. The reaction solution is stirred at 0° C. for 3 h and, after addition of saturated ammonium chloride solution, diluted with water and ethyl acetate, the organic phase is separated off and the aqueous phase is back-extracted twice more with ethyl acetate. The combined organic phases are dried over sodium sulphate and filtered, and the solvent is removed to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). 8.21 g (17.75 mmol, 76% of theory) of a yellowish oil are obtained.

Workup

  1. stirringThe reaction solution is stirred at 0° C. for 3 h
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is back-extracted twice more with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed to dryness
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1)
  8. custom8.21 g (17.75 mmol, 76% of theory) of a yellowish oil are obtained

Sources & evidence

ORD record
ord-d35eb285f556422690119d2b5ad67a7e
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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