Acetone → HCID 66802791, compound

HRID 1057153Notes

Reaction equation

HRID 1057153 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[CH2:14][CH:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12]3)[O:3]1.CC([O-])=O.[NH4+].CC(C)=O>O>[CH2:21]([O:20][C:18]([CH:13]1[CH2:12][C:11]2[C:15](=[CH:16][CH:17]=[C:9]([B:4]([OH:5])[OH:3])[CH:10]=2)[CH2:14]1)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 180AcetoneHCID 517165Ammonium AcetateHCID 66802750HCID 66802750, compound

Product 1

HCID 66802791HCID 66802791, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indene-2-carboxylate (16 g, 50% purity, 25.3 mmol), NaIO4 (24 g, 0.112 mol), CH3COONH4 (5.2 g, 0.068 mol), acetone (100 mL), and water (10 mL) was stirred at room temperature overnight. The acetone was evaporated, and the aqueous residue was extracted with EtOAc (3×100 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound as white solid (3.5 g). 1HNMR (400 MHz, DMSO-d6): δ 7.91 (s, 2H), 7.62 (s, 1H), 7.57 (d, 1H), 7.17 (d, 1H), 4.10 (q, 2H), 3.36-3.32 (m, 1H), 3.09-3.07 (m, 4H), 1.20 (t, 3H).

Workup

  1. customThe acetone was evaporated
  2. extractionthe aqueous residue was extracted with EtOAc (3×100 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cdcc09eface4f4184437e7a428033d3
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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