Potassium sodium tartarate → HCID 59656673, compound

HRID 2054910Notes

Reaction equation

HRID 2054910 reaction equation
[C:1]([C:3]1[C:4]([F:15])=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[C:6](O)=[O:7])#[N:2].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1.CCOCC>[CH2:13]([O:12][C:11]1[C:3]([C:1]#[N:2])=[C:4]([F:15])[C:5]([CH2:6][OH:7])=[CH:9][CH:10]=1)[CH3:14]

Participants

6

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 59656658HCID 59656658, compound

Product 1

HCID 59656673HCID 59656673, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-cyano-4-ethoxy-2-fluorobenzoic acid (3.0 g, 14.34 mmol) in THF (16 mL) and ether (8 mL) at −78° C. was added diisobutylaluminum hydride (DIBAL-H) solution (1 M in THF, 43.0 mL, 43.0 mmol). The reaction was allowed to warm to 0° C. over 3 h, and then it was stored at −10° C. overnight. 1M Sodium potassium tartrate (100 mL, 100 mmol) and diatomaceous earth were added and stirred at room temperature for 4 h. The mixture was filtered through a diatomaceous earth pad, extracted with dichloromethane, rinsed with saturated sodium bicarbonate solution, and rinsed with brine. It was dried over sodium sulfate, concentrated and dried in vacuo to give 6-ethoxy-3-hydroxymethyl-2-fluorobenzonitrile (2.352 g, 12.05 mmol, 63.0%) which was used as is in the next reaction.

Workup

  1. filtrationThe mixture was filtered through a diatomaceous earth pad
  2. extractionextracted with dichloromethane
  3. washrinsed with saturated sodium bicarbonate solution
  4. washrinsed with brine
  5. dry with materialIt was dried over sodium sulfate
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b7f7db05029243e1b3470ef8b06bf78c
Source dataset
uspto-grants-2008_02
Patent number
US07329764B2

Reaction notes

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