Cesium carbonate → (7-Thiocyanato-indan-4-yloxy)-acetic acid methyl ester

HRID 1296035Notes

Reaction equation

HRID 1296035 reaction equation
[S:1]([C:4]1[C:12]2[CH2:11][CH2:10][CH2:9][C:8]=2[C:7]([OH:13])=[CH:6][CH:5]=1)[C:2]#[N:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>C(#N)C>[CH3:25][O:24][C:22](=[O:23])[CH2:21][O:13][C:7]1[CH:6]=[CH:5][C:4]([S:1][C:2]#[N:3])=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 222801707-Thiocyanato-indan-4-ol

Product 1

HCID 20770873(7-Thiocyanato-indan-4-yloxy)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Thiocyanato-indan-4-ol (Example 1B) (3.23 g, 16.89 mmol), cesium carbonate (11 g, 33.8 mmol) and methyl bromoacetate (2.58 g, 16.89 mmol) were stirred in 20 ml acetonitrile at ambient temperature for 4 h. The reaction was filtered and concentrated. The crude product was recrystallized from ethyl acetate/heaxanes to afford the title product. MS m/z 239 (M+1).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe crude product was recrystallized from ethyl acetate/heaxanes

Sources & evidence

ORD record
ord-63984f627429469db3986fdc68249007
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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