HCID 10012697, compound → 2-(2,3-dihydro-1H-inden-2-yl)acetic Acid

HRID 1669117Notes

Reaction equation

HRID 1669117 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]/[C:3]/1=[CH:11]\[C:12]([OH:14])=[O:13]>CO.O1CCOCC1.[Pd]>[CH2:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:2][CH:3]1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 1

HCID 10012697HCID 10012697, compound

Product 1

HCID 51749552-(2,3-dihydro-1H-inden-2-yl)acetic Acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of acid 146 (10.0 g, 53.1 mmol) in MeOH (45 mL) and dioxane (150 mL) with Pd/C (10%, 1.0 g) was stirred under H2 (40 psi) for 16 h. The mixture was filtered through Celite and the solvent evaporated to give acid 147 as an off-white solid: mp 85-88° C. [lit. (Nagasawa et al., Japanese Patent 04338358, 1992) 89-91° C.]; 1H NMR δ 8.47 (br s, 1H, OH), 7.08-7.18 (m, 4H, H-4, H-5, H-6, H-7), 2.99-3.06 (m, 2H, H-1, H-3), 2.69-2.74 (m, 1H, H-2), 2.53-2.60 (m, 2H, H-1, H-3), 2.48 (d, J=7.4 Hz, 2H, CH2CO2).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-ec29599979ad46f99d465151d80ec9bb
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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