1,1'-(Diazomethylene)bis(benzene) → HCID 14901560, compound

HRID 982656Notes

Reaction equation

HRID 982656 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([OH:26])(=[O:25])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18]>CCOC(C)=O>[CH:7]([O:26][C:16](=[O:25])[C@@H:17]([OH:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 439616(S)-mandelic acid

Product 1

HCID 14901560HCID 14901560, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of diphenyldiazomethane (0.528 g, 2.719 mmol) in EtOAc (5 mL) was added portionwise with cooling (ice bath) and stirring to a solution of (S)-mandelic acid (0.500 g, 3.286 mmol) in EtOAc (5 mL). The purple reaction mixture was stirred at room temperature for 1 h and was then washed successively with saturated NaHCO3 (3×5 mL) and brine (2×5 mL), dried over anhydrous MgSO4 and evaporated to 0.9864 g of a yellow solid, which was recrystallized from hexanes to give 0.67 g (80%) of 2g. 1H NMR (400 MHz) in CDCl3 (J, Hz): δ 3.4515 (d, 1H, OH), 5.2782 (d, 1H, CHOH), 6.75 (s, 1H, CHPh2), 7.20-7.45 (m, 15H, ArH).

Workup

  1. temperaturewith cooling (ice bath)
  2. washwas then washed successively with saturated NaHCO3 (3×5 mL) and brine (2×5 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated to 0.9864 g of a yellow solid, which
  5. customwas recrystallized from hexanes

Sources & evidence

ORD record
ord-8895aa21cf7f4b9e8129be4b1f03f650
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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