Boron trifluoride etherate → HCID 69517239, compound

HRID 854861Notes

Reaction equation

HRID 854861 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.B(F)(F)F.[CH3:25]COCC.C(=O)(O)[O-].[Na+].[CH2:35]1[CH2:40][CH2:39]CCC1>>[C:40]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:13])[F:14])[O:9]2)=[CH:4][CH:3]=1)([CH3:39])([CH3:35])[CH3:25]

Participants

5

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8078CyclohexaneHCID 516892Sodium BicarbonateHCID 69517747HCID 69517747, compound

Product 1

HCID 69517239HCID 69517239, compoundYield 56%

Procedure

Ethyl 7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 1a, Step 1 (2.0 g, 6.94 mmole) was treated with t-butyl trichloroacetaimidate in cyclohexane at room temperature. After addition of a catalytic amount of boron trifluoride etherate (139 uL), the mixture (orange solid precipitated) was stirred at room temperature overnight. Solid sodium bicarbonate (2.33 g, 27.76 mmole) was added into the mixture. The mixture was passed through the silica plug and was washed with 6% ethyl acetate in hexane. The filtrate containing the product was evaporated to give yellow oil (1.34 g, 56%) having >90% purity: LCMS m/z 367.00 (M+Na). 1H NMR (CDCl3/400 MHz) 7.70 (s, 1H), 7.12 (m, 1H), 6.63 (s, 1H), 6.61 (m, 1H), 5.68 (q, 1H, J=7.2 Hz), 4.30 (q, 2H, J=7.2 Hz), 1.33 (t, 3H, J=7.2 Hz). This ester was of suitable purity to use without further purification.

Workup

  1. customthe mixture (orange solid precipitated)
  2. washwas washed with 6% ethyl acetate in hexane
  3. additionThe filtrate containing the product
  4. customwas evaporated

Sources & evidence

ORD record
ord-509c1a6310304c63a740c64dc047cf31
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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