Benzyl Alcohol → HCID 178525795, compound

HRID 2202322Notes

Reaction equation

HRID 2202322 reaction equation
[C@H:1]1([C:8]([OH:10])=[O:9])[CH2:4][C@@H:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[CH2:11]([O:6][C:5]([C@@H:3]1[CH2:4][C@H:1]([C:8]([OH:10])=[O:9])[CH2:2]1)=[O:7])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178525793HCID 178525793, compound

Product 1

HCID 178525795HCID 178525795, compoundYield 91.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of cis-cyclobutane-1,3-dicarboxylic acid (4.00 g, 27.75 mmol), benzyl alcohol (2.87 mL, 27.75 mmol) and DMAP (0.339 g, 2.78 mmol) in DMF (80 mL) was added WSC (5.59 mL, 30.53 mmol) at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water, and the pH of the mixture was adjusted to 2 to 3 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give crude cis-3-((benzyloxy)carbonyl)cyclobutanecarboxylic acid (5.93 g, 25.3 mmol, 91%) as a colorless oil. This compound was used for the next step without purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-596500de63fd472a89ffffadf562b700
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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