Methanol → HCID 589496, compound

HRID 1844081Notes

Reaction equation

HRID 1844081 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:11][C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:20]O>O>[CH3:20][O:13][C:12](=[O:14])[CH2:11][CH:3]1[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10954334(1-Oxo-indan-2-yl)-acetic acid

Product 1

HCID 589496HCID 589496, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (1-Oxo-indan-2-yl)-acetic acid (Step 1, 2.00 g) in methanol (10 mL) at 0° C. was added sulphuric acid (2 mL). The solution was stirred for 2 h and then diluted with water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with sat. sodium hydrogenocarbonate, dried and concentrated to give (1-Oxo-indan-2-yl)-acetic acid methyl ester (pale yellow oil, 2.15 g, quantitative). C12H12O3; MW: 204.23; LCMS (method A) RT 1.40 min; ES 227 (25%, MNa+), 205 (25%, MH+), 173 (100%); IR: 2952, 1734, 1710, 1608, 1436 cm−1; 1H NMR (400 MHz, CDCl3) 7.78 (1H, d), 7.61 (1H, t), 7.47 (1H, d), 7.39 (1H, t), 3.70 (3H, s), 3.47 (1H, dd), 2.95-3.08 (2H, m), 2.89 (1H, dd), 2.63 (1H, dt) ppm. The compound was used without further purification for the next step

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with sat. sodium hydrogenocarbonate
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-66c17d0a2c074cf7b6bc37ef1f69209a
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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