Acetic Acid → Methyl 2,2-dimethylchroman-8-carboxylate

HRID 402801Notes

Reaction equation

HRID 402801 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[O:3]1.[Si](C=[N+]=[N-])(C)(C)[CH3:17].C(O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([C:12]([O:14][CH3:17])=[O:13])[CH:6]=[CH:7][CH:8]=2)[O:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 130516922,2-Dimethylchroman-8-carboxylic acid

Product 1

HCID 66765741Methyl 2,2-dimethylchroman-8-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2,2-dimethyl-3,4-dihydro-2H-chromene-8-carboxylic acid (300 mg, 1.45 mmol) in methanol (2.10 mL) and toluene (5.20 mL) cooled to 0° C. was added TMS-diazomethane (1.82 mL, 3.64 mmol) dropwise via a syringe. The reaction mixture was warmed to room temperature and stirred for 45 minutes. It was then cooled to 0° C., and acetic acid (2.00 mL) was added carefully. The solvent was evaporated under vacuum and the residue was re-dissolved in EtOAc (80.0 mL), washed with a saturated NaHCO3 solution (20.0 mL, dried over Na2SO4, filtered and concentrated under vacuum. The crude product was used directly to the next step without further purification.

Workup

  1. temperatureIt was then cooled to 0° C.
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe residue was re-dissolved in EtOAc (80.0 mL)
  4. washwashed with a saturated NaHCO3 solution (20.0 mL
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude product was used directly to the next step without further purification

Sources & evidence

ORD record
ord-a92e2224055349628d4a87d275872cec
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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