Benzyl Alcohol → HCID 23331768, compound

HRID 224665Notes

Reaction equation

HRID 224665 reaction equation
[C:1]([C:9]1[CH:13]=[C:12]([CH3:14])[N:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[C:10]=1[CH3:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:36](O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[C:1]([C:9]1[CH:13]=[C:12]([CH3:14])[N:11]([CH:15]([CH3:19])[C:16]([O:18][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:17])[C:10]=1[CH3:20])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 23331713HCID 23331713, compound

Product 1

HCID 23331768HCID 23331768, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

In 5 ml of methylene chloride was dissoved 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)propionic acid (500 mg, 1.85 mmoles), and 257 μl (1.85 mmoles) of triethylamine was added. The mixture was stirred at -15° C. for 5 minutes. Isobutyl chloroformate (243 μl, 1.85 mmoles) was added to the solution, and the mixture stirred at -15° C. for 10 minutes. Then, 190 μl (1.85 mmoles) of benzyl alcohol was added. The mixture was stirred at room temperature for 20 hours, and 50 ml of methylene chloride was added. The organic layer was washed with water, dilute hydrochloric acid and an aqueous solution of sodium hydrogen carbonate in this order, dried, and concentrated to afford 543 mg of a crude product. The product was chromatographed on a column of silica gel using benzene/ethyl acetate as an eluent to afford compound (720)(421 mg, 1.16 mmoles, 63%).

Workup

  1. additionwas added
  2. stirringthe mixture stirred at -15° C. for 10 minutes
  3. stirringThe mixture was stirred at room temperature for 20 hours
  4. washThe organic layer was washed with water, dilute hydrochloric acid
  5. dry with materialan aqueous solution of sodium hydrogen carbonate in this order, dried
  6. concentrationconcentrated
  7. customto afford 543 mg of a crude product
  8. customThe product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-2cec35b7c8e247b1b75231e42e4864f0
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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