Ammonium Chloride → Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

HRID 514154Notes

Reaction equation

HRID 514154 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:26])[C:8]([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-]>CCO.C(Cl)Cl.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:26])[C:8]([CH:19]([OH:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]2[C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67126202Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

Product 1

HCID 67126265Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetateYield 107.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methyl-naphthalen-2-yl)-2-oxoacetate (26 mg, 67 μmol) in EtOH (absolute, 1.0 mL) and DCM (1.0 mL) was treated with NaBH4 (5.1 mg, 0.134 mmol) at 23° C. After 1 h, saturated NH4Cl (1.0 mL) was added. The reaction was stirred overnight, then diluted with H2O (10 mL). The mixture was extracted with DCM (3×), and the combined organics dried (Na2SO4), filtered, and concentrated, giving the title compound (28 mg, >99% yield). 1H-NMR: (400 MHz, CDCl3): δ 7.72 (d, J=8.6 Hz, 1H), 7.65 (s, 1H), 7.51-7.22 (m, 6H), 5.19 (s, 1H), 4.35-4.17 (m, 2H), 2.49 (s, 3H), 1.20 (t, J=7.0 Hz, 3H).

Workup

  1. extractionThe mixture was extracted with DCM (3×)
  2. dry with materialthe combined organics dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82bba1ff46bc4a6d9329eb09ad894a49
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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