Ethanol hydrochloride → HCID 10308395, compound

HRID 1835990Notes

Reaction equation

HRID 1835990 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=[O:19])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1.Cl.[CH3:22][CH2:23]O>>[CH2:22]([O:19][C:18]([C:4]1[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=[C:2]([OH:1])[CH:3]=1)=[O:20])[CH3:23]

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 22221627HCID 22221627, compound

Product 1

HCID 10308395HCID 10308395, compoundYield 92%

Procedure

A solution of carboxylic acid 24 (3.5 g, 13 mmol) in HCl/EtOH(100 ml) was refluxed for 2 hr. The reaction was then cooled, concentrated and the product was dissolved in EtOAc, washed with sat NaHCO3, dried over MgSO4, and concentrated to give a solid. The solid was triturated with CH2Cl2, filtered to give the desired product (3.5 g, 92%); Mp=221-223° C.; 1NMR (DMSO-d6) δ 9.90 (s, 1 H), 9.55(s, 1 H), 7.73 (d, 2 H, J=8.5 Hz), 7.23 (d, 1 H, J=2.1 Hz), 7.17 (d. 1 H, J=2.5 Hz), 7.12 (s,1 H), 6.88 (d, 2 H, J=8.5 Hz), 4.43-4.35 (m, 2 H), 1.41 (t, 3 H, J=7.0 Hz); MS 297 (M−H)−.

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated
  3. dissolutionthe product was dissolved in EtOAc
  4. washwashed
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid was triturated with CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-f1e49d7ae19d402aa68fc094d21db421
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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