Diethyl Ether → HCID 22270422, compound

HRID 133444Notes

Reaction equation

HRID 133444 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)C(OC)=O)=[CH:4][CH:3]=1.[CH3:21][Mg]Br.[Cl-].[NH4+].CC[O:28][CH2:29][CH3:30]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[C:29]([CH3:30])([OH:28])[CH3:21])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 22270406Methyl 2,3-bis(4-chlorophenyl)propionateHCID 178418573HCID 178418573, compound

Product 1

HCID 22270422HCID 22270422, compound

Procedure

To a solution of methyl 2,3-bis(4-chlorophenyl)propionate (2.6 g, 8.4 mmol) in ether (20 mL) was added methylmagnesium bromide (3 M in ether, 8.4 mL, 25 mmol) at −10° C., and the reaction was allowed to warm to room temperature over 2 h. The reaction mixture was poured into saturated aqueous ammonium chloride (100 mL), and the product was extracted with EtOAc (3×100 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.17 (ABq, 4H), 7.06 (d, 2H), 6.93 (d, 2H), 3.32 (dd, 1H), 2.94 (dd, 1H), 2.84 (dd, 1H), 1.20 (s, 3H), 1.16 (s, 3H).

Workup

  1. extractionthe product was extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined extracts were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-db51f058a97146cdbb53de89fd4a28af
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Reaction notes

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