Triethylamine → TCO-carbonate

HRID 1395874Notes

Reaction equation

HRID 1395874 reaction equation
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:17]1[C:22](=[O:23])[N:21]([O:24][C:25](ON2C(=O)CCC2=O)=[O:26])[C:19](=[O:20])[CH2:18]1>C(#N)C>[C:25](=[O:26])([O:24][N:21]1[C:22](=[O:23])[CH2:17][CH2:18][C:19]1=[O:20])[O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 1238561585081-69-2

Product 1

HCID 58490201TCO-carbonateYield 75.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

50 mg of (E)-cyclooct-4-enol (major isomer) and 0.2 mL triethylamine were added to 3 mL anhydrous acetonitrile. To this solution was slowly added 250 mg of N,N-disuccinimidyl carbonate. The reaction mixture was stirred at room temperature until thin layer chromatography revealed that the reaction was complete (approximately 48 hours). The acetonitrile was removed by rotary evaporation and the remaining residue was suspended in ether, washed with 0.1M HCl followed by brine, and dried with magnesium sulfate. The ether was evaporated and the resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane) yielding 80 mg (75% yield) of the title compound. 1H NMR (400 MHz CDCl3): δ 5.65-5.54 (m, 1H), 5.5-5.4 (m, 1H), 4.5-4.4 (m, 1H), 2.88-2.78 (s, 4H), 2.45-2.3 (m, 2H), 2.2-1.5 (m, 8H).

Workup

  1. custom(approximately 48 hours)
  2. customThe acetonitrile was removed by rotary evaporation
  3. washwashed with 0.1M HCl
  4. dry with materialdried with magnesium sulfate
  5. customThe ether was evaporated
  6. customthe resulting oil was purified by column chromatography (1:1 Ethyl Acetate:Hexane)

Sources & evidence

ORD record
ord-332f52934dc843b5b4a74acaacd6b278
Source dataset
uspto-grants-2014_12
Patent number
US08900549B2

Reaction notes

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