Acetic Anhydride → HCID 19106822, compound

HRID 1197478Notes

Reaction equation

HRID 1197478 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[C:11](OC(=O)C)(=O)C>O>[CH2:11]=[C:7]1[CH2:8][CH2:9][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]1=[O:10]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphthene

Product 1

HCID 19106822HCID 19106822, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
122 °C

Procedure

To 20.0 mL of tetramethyldiaminomethane was added 10.0 g of 6,7-dihydrobenzo[b]thiophen-4(5H)-one all at once. To this mixture was added 20.0 mL of acetic anhydride, dropwise. The reaction mixture exothermed to 45° C. and was heated to 122° C. for 15 minutes and then cooled to 90° C. where it was kept for 60 minutes. The dark solution was poured into cold water and extracted with ether. The ether was extracted with a saturated solution of NaHCO3 and then washed with brine. The ether layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a yellow oil. The yellow oil was flash-chromatographed using 10% ethyl acetate and 90% hexanes as eluent to afford 6.18 g of a white solid, m.p. 47°-49° C. 200 MHz1H NMR(CDCl3) δ2.97 (t, 2H), 3.07 (t, 2H), 5.46 (s, 1H), 6.17 (s,1H), 7.11 (d, 1H), 7.48 (d, 1H); I. R. (Nugol) 1660 cm-1.

Workup

  1. customexothermed to 45° C.
  2. temperaturecooled to 90° C. where it
  3. extractionextracted with ether
  4. extractionThe ether was extracted with a saturated solution of NaHCO3
  5. washwashed with brine
  6. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a yellow oil
  10. customThe yellow oil was flash-chromatographed

Sources & evidence

ORD record
ord-12e47ea6b2ca4335b8444b3a415d44a1
Source dataset
uspto-grants-1994_01
Patent number
US05276039

Reaction notes

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