Methanol → HCID 14552599, compound

HRID 1073398Notes

Reaction equation

HRID 1073398 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1.[OH-:22].[K+].[BH4-].[Na+].[CH3:26]O>>[CH3:26][O:22][C:2]([CH3:1])([CH3:21])[CH2:3][CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 887Methanol4×HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 14552588HCID 14552588, compound

Product 1

HCID 14552599HCID 14552599, compound

Procedure

To ethyl N-{2-[4-(3-methyl-2-butenoxy)phenoxy]ethyl}carbamate (0.60 g, 2.05 mmol) in methanol (7 ml) at ~40° is added mercuric acetate (0.67 g, 2.1 mmol) in methanol (8 ml) over 10 min. The mixture is stirred at 5° for 1 hour, then at 10°-15° for 30 min. Additional mercuric acetate (0.13 g, 0.41 mol) in methanol is added, and the mixture is allowed to stand at RT overnight. The mixture is then cooled to 3° and potassium hydroxide (0.57 g, 10.2 mmol) in methanol (4 ml) is added over 5 min., followed by addition of sodium borohydride (0.039 g, 1.02 mmol) in portions over 10 min. The resulting slurry is stirred at 3°-5° for 45 min. Celite is added to the reaction mixture and the mercury is filtered off. Methanol is removed by rotoevaporation and ether and water are added to the residue. Following extraction with ether (3×), the ether extracts are combined and washed with water until neutral and with brine and dried over calcium sulfate. The crude product is filtered, rotoevaporated and purified by prep. TLC to yield ethyl N-{2-[4-(3-methoxy-3-methylbutoxy)phenoxy]ethyl}carbamate (compound 12, Table A).

Workup

  1. waitat 10°-15° for 30 min
  2. waitto stand at RT overnight
  3. temperatureThe mixture is then cooled to 3°
  4. stirringThe resulting slurry is stirred at 3°-5° for 45 min
  5. additionCelite is added to the reaction mixture
  6. filtrationthe mercury is filtered off
  7. customMethanol is removed by rotoevaporation and ether and water
  8. additionare added to the residue
  9. extractionextraction with ether (3×)
  10. washwashed with water until neutral and with brine
  11. dry with materialdried over calcium sulfate
  12. filtrationThe crude product is filtered
  13. custompurified by prep

Sources & evidence

ORD record
ord-fa7e90ea7c764af3b7d262e6c9e7237b
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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