Acetic Anhydride → HCID 86602830, compound

HRID 1444703Notes

Reaction equation

HRID 1444703 reaction equation
[C@H:1]1([NH:11][CH:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(OC(=O)C)(=[O:16])C>>[O:16]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C@H:1]([NH:11][CH:12]=[O:13])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 86602829HCID 86602829, compound

Product 1

HCID 86602830HCID 86602830, compound

Conditions

Temperature
0 °C

Procedure

To a solution of (R)—N-(1,2,3,4-tetrahydronaphthalen-1-yl)formamide (4.01 g, 22.9 mmol) in 40 mL of acetic anhydride at 0° C. was added Chomium(VI) oxide (6.00 g, 60.0 mmol). The solution was stirred at 0° C. for 1 h. The solution was filtered, extracted with EtOAc, washed with brine, dried over Na2SO4 and evaporated to dryness. flash chomatograph (SiO2, EtOAc/hexane=1:1 to 2:1 to pure EtOActo EtOAc/MeOH=10:1 to 10:2) afforded (R)—N-(4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl)formamide as a white solid.

Workup

  1. filtrationThe solution was filtered
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-00c6337aef5d484c811aee5bbe81a235
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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