Hydrochloric Acid → 2-(2-Benzyloxyethyl)acrylic acid tert-butyl ester

HRID 1459883Notes

Reaction equation

HRID 1459883 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH:7]([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8](O)=O)([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.C=O.Cl>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:21])[C:7]([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH2:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 186910232-(2-Benzyloxyethyl) malonic acid mono tert-butyl ester

Product 1

HCID 539165622-(2-Benzyloxyethyl)acrylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(2-benzyloxyethyl) malonic acid mono tert-butyl ester (23.9 g, 81.2 mmol), piperidine (1.31 mL, 13.2 mmol), and paraformaldehyde (3.7 g, 123 mmol) in pyridine (160 mL) was heated at a temperature of 70° C. for 3 hours. After cooling to room temperature, the mixture was poured over ice. The mixture was acidified using 6N HCl solution and then extracted twice with ether; the extracts were combined, washed with brine, dried over MgSO4 and concentrated under vacuum to leave an oil. The oil was chromatographed on silica gel using 6% ethyl acetate in hexane to afford 2-(2-benzyloxyethyl)acrylic acid tert-butyl ester as a clear oil, 18.51 g (87%).

Workup

  1. additionthe mixture was poured over ice
  2. extractionextracted twice with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customto leave an oil
  7. customThe oil was chromatographed on silica gel using 6% ethyl acetate in hexane

Sources & evidence

ORD record
ord-896e718ccfd6429bb7748356f3389994
Source dataset
uspto-grants-1998_12
Patent number
US05854275

Reaction notes

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