Acetic Acid → HCID 69931650, compound

HRID 1637804Notes

Reaction equation

HRID 1637804 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C:19]3[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=3)[O:13][CH2:12][C@H:11]2[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)[CH:6]=[CH:7][C:8]=1[OH:9].[CH2:29](N(CC)CC)[CH3:30].C(O)(=O)C>O>[CH3:21][O:20][C:16]1[CH:15]=[C:14]2[C:19]([C@H:10]([C:5]3[CH:6]=[CH:7][C:8]4[O:9][C:29]([CH3:30])=[N:2][C:3]=4[CH:4]=3)[C@H:11]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[CH2:12][O:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 131721743HCID 131721743, compound

Product 1

HCID 69931650HCID 69931650, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of (±)-cis4-(3-amino-4-hydroxyphenyl)-7-methoxy-3-(4-methylphenyl)-chromane hydrochloride (0.475 g, 1.19 mmol), triethylamine (0.173 ml, 1.25 mmol) and acetic acid (15 ml) was heated to gentle reflux for 18 h., giving a deep red coloured mixture. This was cooled to room temperature, poured into water (100 ml) and the product extracted into ethyl acetate (2×100 ml). The combined extracts were washed with water (6×50 ml), brine, dried over magnesium sulfate and evaporated to give a dark gum. This was purified by column chromatography on silica gel 60, with a 1:1 petrol/ethyl acetate eluent. This gave the product, on vacuum drying, as a stable pale pink coloured foam.

Workup

  1. temperaturewas heated
  2. temperatureto gentle reflux for 18 h.
  3. customgiving a deep red
  4. extractionthe product extracted into ethyl acetate (2×100 ml)
  5. washThe combined extracts were washed with water (6×50 ml), brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a dark gum
  9. customThis was purified by column chromatography on silica gel 60, with a 1:1 petrol/ethyl acetate eluent
  10. customThis gave the product
  11. customon vacuum drying, as a stable pale pink coloured foam

Sources & evidence

ORD record
ord-2dffc986848440518576dfca1bf876ab
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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