Acetic Anhydride → HCID 15490889, compound

HRID 1954259Notes

Reaction equation

HRID 1954259 reaction equation
[CH3:1][C:2]1[S:6][C:5]2[CH:7]=[C:8]3[C:13](=[C:14]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH:22]([CH3:24])[CH3:23])[CH:16]=4)[C:4]=2[C:3]=1[CH3:25])[CH:12]=[CH:11][CH:10]=[CH:9]3.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1>[CH:22]([C:17]1[CH:16]=[C:15]([C:14]2[C:4]3[C:3]([CH3:25])=[C:2]([CH3:1])[S:6][C:5]=3[CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:20]=[CH:19][C:18]=1[O:21][C:26](=[O:28])[CH3:27])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15490888HCID 15490888, compound

Product 1

HCID 15490889HCID 15490889, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 5° C., to a stirred solution of 4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-isopropyl-phenol (0.500 g, 1.44 mmol) in pyridine (3.5 mL) was added acetic anhydride (0.167 mL, 1.78 mmol). After 5.5 h, the reaction was quenched with H2O, acidified and extracted with ether. The combined ethereal extracts were sequentially washed with H2O, brine and concentrated. Purification on silica gel, eluting with 5 & 7% EtOAc/pet. ether, step gradient gave 0.384 g (69%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 8.49 (s, 1 H), 8.00-7.96 (d, 1 H), 7.48-7.31 (m, 4 H), 7.20 (s, 2 H), 3.10 (septet, 1 H), 2.40 (s, 3 H), 2.37 (s, 3 H), 1.56 (s, 3 H), 1.16 (d, 6 H).

Workup

  1. customthe reaction was quenched with H2O
  2. extractionextracted with ether
  3. washThe combined ethereal extracts were sequentially washed with H2O, brine
  4. concentrationconcentrated
  5. customPurification on silica gel
  6. washeluting with 5 & 7% EtOAc/pet. ether, step gradient

Sources & evidence

ORD record
ord-b22e7cc18ee24835977c81157880a70f
Source dataset
uspto-grants-2000_09
Patent number
US06121271

Reaction notes

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