Potassium Hydroxide → HCID 11337688, compound

HRID 646808Notes

Reaction equation

HRID 646808 reaction equation
[OH-:1].[K+].C([O:5][C:6](=[O:43])[C:7]([CH3:42])([CH3:41])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([N+]#[C-])(S(C1C=CC(C)=CC=1)(=O)=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([O:24]CC)=[O:23])C>O.C(O)C>[CH3:41][C:7]([CH3:42])([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:1])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[C:22]([OH:24])=[O:23])[C:6]([OH:5])=[O:43]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 11387750HCID 11387750, compound

Product 1

HCID 11337688HCID 11337688, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of KOH (85%, 8.4 g, 127.3 mmol) in deionized water (3.6 mL) and ethanol (11.5 mL) was added 208i (15.0 g, 25.3 mmol) and the mixture was heated to reflux for 7 h. The reaction mixture was diluted with water (40 mL) and extracted with MTBE (2×30 mL). The aqueous layer was cooled with an ice-bath and the pH was adjusted to 1 by addition of 5 N sulfuric acid (45 mL). The aqueous layer was extracted with MTBE (3×30 mL) and the combined organic layers were washed with brine (50 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give a crude oil (12.5 g). Purification by chromatography (silica gel, ethyl acetate/hexanes=10% to 100%) and recrystallization from MTBE/hexanes (4 mL/50 mL) yielded 210i (5.37 g, 57%) as a white powder. Mp 74.5-76.0° C. 1H NMR (CDCl3): δ (ppm): 12.40-11.20 (br, 2H), 2.39 (t, J=7.3, 4H), 1.62-1.48 (m, 8H), 1.38-1.22 (m, 12H), 1.11 (s, 12H). 13C NMR (CDCl3=77.02 ppm): δ (ppm): 211.88, 184.93, 42.70, 42.19, 40.63, 29.63, 29.09, 24.96, 24.83, 23.83. HRMS (LSIMS, gly): Calcd for C21H39O5 (MH+): 371.2797, found: 371.2804.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 7 h
  3. extractionextracted with MTBE (2×30 mL)
  4. temperatureThe aqueous layer was cooled with an ice-bath
  5. additionthe pH was adjusted to 1 by addition of 5 N sulfuric acid (45 mL)
  6. extractionThe aqueous layer was extracted with MTBE (3×30 mL)
  7. washthe combined organic layers were washed with brine (50 mL)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a crude oil (12.5 g)
  11. customPurification
  12. customby chromatography (silica gel, ethyl acetate/hexanes=10% to 100%) and recrystallization from MTBE/hexanes (4 mL/50 mL)

Sources & evidence

ORD record
ord-ee47a127dd9748d5a8f82b0fb0a697bf
Source dataset
uspto-grants-2010_04
Patent number
US07705177B2

Reaction notes

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