Triethylamine → HCID 54148061, compound

HRID 2421636Notes

Reaction equation

HRID 2421636 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.C[Si]([CH:31]=[N+:32]=[N-:33])(C)C>>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[CH:14][CH:13]=[C:9]([C:10](=[O:12])[CH:31]=[N+:32]=[N-:33])[CH:8]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 24386Thionyl ChlorideHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 54148061HCID 54148061, compoundYield 21%

Conditions

Temperature
60 °C

Procedure

A mixture of 3-phenylbenzoic acid (595 mg, 3 mmol) and thionyl chloride (1 mL) was heated at 60° C. for 2.5 hours. After this time, the thionyl chloride was removed under vaccum. Toluene was then added and the resulting solution was concentrated. This procedure was repeated two more times. The oily residue was then dissolved in dry THF. At 0° C., triethylamine (304 μL, 3 mmol) and trimethylsilyldiazomethane were added successively. The reaction was then stirred for 20 hours at room temperature. The reaction was concentrated. Purification of the residue by flash chromatography using CH2Cl2/AcOEt 95:5 to 85:15 gave the compound as a yellow thick oil (141 mg, 21%). NMR 1H (ppm, CDCl3): 7.98 (t., J3=1.37 Hz, 1H), 7.74-7.67 (m, 2H), 7.60-7.57 (m, 2H), 7.50-7.24 (m, 4H), 5.95 (s, 1H). MS (+ESI): M+H+: 222.9.

Workup

  1. customAfter this time, the thionyl chloride was removed under vaccum
  2. additionToluene was then added
  3. concentrationthe resulting solution was concentrated
  4. dissolutionThe oily residue was then dissolved in dry THF
  5. concentrationThe reaction was concentrated
  6. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-fddea4444b0247489474812e98c64bb9
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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