Ammonium Chloride → HCID 54053136, compound

HRID 2210784Notes

Reaction equation

HRID 2210784 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:9][C:10](=[O:26])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:24][OH:25])[CH3:8].[CH:27](Br)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl-].[NH4+]>CN(C)C=O.CCOCC>[CH2:7]([O:9][C:10](=[O:26])[CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:24][O:25][CH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:8]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 236603BromodiphenylmethaneHCID 23665647Potassium tert-butoxideHCID 54405952HCID 54405952, compound

Product 1

HCID 54053136HCID 54053136, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (810 mg) was added to a solution of [1-(2-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-5-yloxy]acetic acid ethyl ester (2.11 g, prepared by the same procedure as in reference example 1) in dimethylformamide (50 ml) at 0° C. The reaction mixture was stirred for 1 hr at room temperature. Benzhydryl bromide (2.15 g) was added to the mixture at 0° C. The mixture was stirred for 1 hr at room temperature. To the mixture, a saturated aqueous solution of ammonium chloride and ether were added. The extract was washed with water and saturated brine, dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=8: 2) to give the title compound (257 mg).

Workup

  1. stirringThe mixture was stirred for 1 hr at room temperature
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=8: 2)

Sources & evidence

ORD record
ord-ccb5ff88518547f08a9e6df1bdc9193d
Source dataset
uspto-grants-1995_10
Patent number
US05461045

Reaction notes

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