Water → HCID 69199600, compound

HRID 2252237Notes

Reaction equation

HRID 2252237 reaction equation
[CH:1](OCC)=[O:2].[H-].[Na+].[CH3:8][O:9][C:10]1[CH:18]=[C:17]2[C:13]([CH2:14][CH2:15][C:16]2=[O:19])=[CH:12][CH:11]=1.O>C1C=CC=CC=1>[OH:2][CH:1]=[C:15]1[CH2:14][C:13]2[C:17](=[CH:18][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)[C:16]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 3340366-Methoxy-1-Indanone

Product 1

HCID 69199600HCID 69199600, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of ethyl formate (15.75 mL, 0.195 mol) and NaH (60%, 7.80 g, 0.195 mol) in benzene (550 mL) was added a suspension of 6-methoxy-indan-1-one (15.81 g, 0.0974 mol) in benzene (150 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature overnight and treated with water. The solid was filtered, washed with water, and oven dried to give the desired product (16.86 g, 91%). The product may exist in sodium salt form, however, it was carried into the next reaction without further characterization. MS (DCI/NH3) m/z: 191.1 (M+H)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 3.50 (s, 2H) 3.80 (s, 3H) 7.13-7.20 (m, 2H) 7.47 (d, J=8.14 Hz, 1H) 7.74 (s, brd, 1H).

Workup

  1. additionwas added
  2. filtrationThe solid was filtered
  3. washwashed with water, and oven
  4. customdried

Sources & evidence

ORD record
ord-f92fa25e67e74244afe60b5de043f96f
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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