2-Ethyl-1-butanol → HCID 69517745, compound

HRID 854870Notes

Reaction equation

HRID 854870 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[C:30]([CH3:31])=[C:29]2[C:24]([CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[CH:27]([C:32]([F:35])([F:34])[F:33])[O:28]2)=[CH:23][CH:22]=1.[CH2:40]([CH:42]([CH2:45][CH3:46])[CH2:43]O)[CH3:41].N(C(OCC)=O)=NC([O-])=O>C1COCC1>[CH2:40]([CH:42]([CH2:45][CH3:46])[CH2:43][O:20][C:21]1[C:30]([CH3:31])=[C:29]2[C:24]([CH:25]=[C:26]([C:36]([O:38][CH3:39])=[O:37])[CH:27]([C:32]([F:35])([F:33])[F:34])[O:28]2)=[CH:23][CH:22]=1)[CH3:41]

Participants

6

Reactant 4

HCID 73582-Ethyl-1-butanolHCID 11776TriphenylphosphineHCID 69516883methyl 7-hydroxy-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 69517745HCID 69517745, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Polymer bound PPh3 was suspended in THF for 15 min. Methyl 7-hydroxy-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Step 1 (1.5 g, 5.21 mmole) and 2-ethyl butanol (0.96 mL, 7.81 mmole) were added to the above slurry and stirred for 15 min. Ethyl azodicarboxylate (1.23 mL, 7.81 mmole) was added to above mixture dropwise and the mixture was stirred at room temperature overnight. LCMS indicated product formation and that there was no starting material present. The polymer was filtered off through celite pad and the pad was washed with ether. The filtrate was concentrated and the product mixture was suspended in hexane. The undissolved solid was removed by filtration and the filtrate was evaporated and dried in vacuo to afford yellow solid, (1.76 g, 98%): LCMS m/z395.15 (M+Na). 1H NMR (CDCl3/400 MHz) 7.68 (s, 1H), 7.00 (d, 1H, J=8.4 Hz), 6.48 (d, 1H, J=8.4 Hz), 5.68 (q, 1H, J=7.2 Hz), 3.89 (m, 2H), 3.82 (s, 3H), 2.09 (s, 3H), 1.72 (m, 1H), 1.53 (m, 4H), 0.95 (m, 6H). This ester was of suitable purity to use without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationThe polymer was filtered off through celite pad
  3. washthe pad was washed with ether
  4. concentrationThe filtrate was concentrated
  5. customThe undissolved solid was removed by filtration
  6. customthe filtrate was evaporated
  7. customdried in vacuo
  8. customto afford yellow solid, (1.76 g, 98%)
  9. customto use without further purification

Sources & evidence

ORD record
ord-f8b1e96440804089968478409072b215
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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