2-Ethyl-1-butanol → HCID 69517841, compound

HRID 854860Notes

Reaction equation

HRID 854860 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:20][C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]([C:31]([F:34])([F:33])[F:32])[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[CH:30]=[C:29]2[C:24]([CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]([C:31]([F:34])([F:32])[F:33])[O:28]2)=[CH:23][CH:22]=1)[CH3:41]

Participants

6

Reactant 4

HCID 73582-Ethyl-1-butanolHCID 11776TriphenylphosphineHCID 69517747HCID 69517747, compoundHCID 86599450N-ethoxycarbonyliminocarbamate

Product 1

HCID 69517841HCID 69517841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The polymer bound PPh3 was suspended in THF for 15 min. Ethyl 7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 1a, Step 1 (2.0 g, 6.94 mmole) and 2-ethyl-1-butanol (1.3 mL, 10.35 mmole) were added to above slurry and the mixture was stirred at r.t. for 15 min. Ethyl azodicarboxylate (1.6 mL, 10.35 mmole) was added to above mixture dropwise and the mixture was stirred at room temperature overnight. LCMS indicated product formation and that there was a trace amount of 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 suspension was filtered and the filtrate was evaporated and dried in vacuo to afford yellow oil, (2.37 g, 92%): LCMS m/z 394.95 (M+Na). 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. filtrationThe suspension was filtered
  6. customthe filtrate was evaporated
  7. customdried in vacuo
  8. customto afford yellow oil, (2.37 g, 92%)
  9. customto use without further purification

Sources & evidence

ORD record
ord-4a7d2c73a6e14a4aaa96fc7ec1b33456
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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