Hydrochloric Acid → HCID 11153766, compound

HRID 855165Notes

Reaction equation

HRID 855165 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[O:8][CH:7]([C:21]([F:24])([F:23])[F:22])[C:6]([C:25]([O:27]CC)=[O:26])=[CH:5]2.[OH-].[Li+].Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=1)[O:8][CH:7]([C:21]([F:24])([F:22])[F:23])[C:6]([C:25]([OH:27])=[O:26])=[CH:5]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58934933HCID 58934933, compound

Product 1

HCID 11153766HCID 11153766, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.43 g (10.4 mmole) of the product of step 1 in 70 mLs of THF and 20 mL of methanol was added a solution of 1.0 g of lithium hydroxide monohydate in 10 mL of water. The mixture was heated to reflux for 30 min and allowed to cool to rt. After stirring overnight, the mixture was treated with 75 mL of 1N HCl and extracted three times with diethyl ether. The combined extracts were washed with brine, dried and concd in vacuo to afford 4.02 g (97%) of a yellow solid: mp 195.5-196.5° C.; 1H NMR (d6-acetone/400 MHz) 1.22 (t, 3H, J=7.5 Hz), 2.66 (q, 2H, J=7.6 Hz), 5.78 (q, 1H, J=7.1 Hz), 6.45 (s, 1H), 7.04 (d, 2H, J=8.4 Hz), 7.31 (d, 2H, J=8.3 Hz), 7.66 (s, 1 H), 7.87 (s, 1H); 19F NMR (d6-acetone/400 MHz) −79.4 (d, 3F, J=7.7 Hz); 13C NMR (d6-acetone/100 MHz) 15.4, 28.1, 70.9 (q, J=32.7 Hz), 105.6, 115.3, 116.0, 117.5, 119.9, 123.9 (q, J=286.8 Hz), 129.8, 131.1, 135.7, 141.5, 153.1, 153.3, 157.3, 164.3; MS (ES−) 397 (M−1, 100); HRMS (ES−) m/z calcd for (C19H13ClF3O4) 397.0449, found 397.0484.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min
  3. extractionextracted three times with diethyl ether
  4. washThe combined extracts were washed with brine
  5. customdried

Sources & evidence

ORD record
ord-a2c4f6e8694c49f8a177cf4a156ae1dc
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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