Borane;tetrahydrofuran → HCID 18787383, compound

HRID 342079Notes

Reaction equation

HRID 342079 reaction equation
B.C1COCC1.[CH2:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=1[CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])=[O:11])[CH3:8]>C1COCC1>[CH2:7]([O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=1[CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18787496HCID 18787496, compound

Product 1

HCID 18787383HCID 18787383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane THF complex (56 ml of 1M in THF, 56 mmol) was slowy added to a solution of 4-[2-ethoxycarbonyl-6-hydroxyphenyl]butanoic acid in THF at 0° C. The solution was stirred for 2 hr and allowed to warm to room temperature. The reaction was quenched slowly with aqueous acetic acid (5 ml of 50%) and stirred until the bubbling subsided. The mixture was concentrated in vacuo to a slurry, which was dissolved in cold 10% potassium carbonate. The solution was extracted with ethyl acetate twice. The organic extracts were dried with brine and concentrated in vacuo to a tan oil that solidified upon standing (5.14 g, 84.9%).

Workup

  1. customThe reaction was quenched slowly with aqueous acetic acid (5 ml of 50%)
  2. stirringstirred until the bubbling
  3. concentrationThe mixture was concentrated in vacuo to a slurry, which
  4. dissolutionwas dissolved in cold 10% potassium carbonate
  5. extractionThe solution was extracted with ethyl acetate twice
  6. dry with materialThe organic extracts were dried with brine
  7. concentrationconcentrated in vacuo to a tan oil that

Sources & evidence

ORD record
ord-8886ed1167b44b3cb035158bc5175112
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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