HCID 12947566, compound → HCID 12906775, compound

HRID 1449245Notes

Reaction equation

HRID 1449245 reaction equation
C[O:2][C:3]1(OC)[CH2:12][CH2:11][CH:10]2[C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)([CH2:6][CH2:7][N:8]([CH3:13])[CH2:9]2)[CH2:4]1>C(O)(=O)C>[CH3:21][O:20][C:16]1[CH:15]=[C:14]([C:5]23[CH2:4][C:3](=[O:2])[CH2:12][CH2:11][CH:10]2[CH2:9][N:8]([CH3:13])[CH2:7][CH2:6]3)[CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 12947566HCID 12947566, compound

Product 1

HCID 12906775HCID 12906775, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ketal 49 (Example 31) (50 mg, 0.158 mmol) was dissolved in 2 mL of 3 N acetic acid and stirred for 4 h. Basification (pH 8.5), extraction with CHCl3 (2×5 mL), drying, and evaporation gave 29 mg (68%) of 41 as an oil. Attempted distillation resulted in decomposition and 41 failed to form a crystalline methiodide: NMR δ 7.27 (t, J=7 Hz, 1H), 6.77 (m, 3H), 5.96 (m, 1H), 3.78 (s, 3H), 2.27 (s, 3H); IR 1715, 1595, 1578 cm-1 ; mass spectrum m/e (rel intensity) 271 (100), 215 (43), 164 (48), 71 (55), 70 (41). C17H18NO2 requires 271.1572; found 271.1563.

Workup

  1. extractionBasification (pH 8.5), extraction with CHCl3 (2×5 mL)
  2. customdrying
  3. customevaporation

Sources & evidence

ORD record
ord-1d40cbe0acfd402abe4e0c39641e8056
Source dataset
uspto-grants-1980_02
Patent number
US04189583

Reaction notes

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