Methanol → HCID 71256597, compound

HRID 1428978Notes

Reaction equation

HRID 1428978 reaction equation
[CH3:1][C:2]1([CH3:22])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19](O)=[O:20])=[CH:11][CH:10]=2)[O:3]1.B.CO>C1COCC1>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:22])[O:3][B:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][OH:20])=[CH:11][CH:10]=2)[O:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 467387444-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-1-carboxylic acid

Product 1

HCID 71256597HCID 71256597, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthoic acid (2.5 g, 8.39 mmol) was dissolved in anhydrous THF. The solution was cooled down in an ice-water bath. Borane solution (1.00M in THF, 25 ml, 25 mmol) was added dropwise. After addition, the reaction was stirred at room temperature for 4 hours. Methanol (20 ml) was added with ice-water batch to quench the reaction until no gas was produced. The solvent was evaporated, and the residue was extracted with ethyl acetate/water to give the product as a white solid (1.79 g, 75%). 1H NMR (300 MHz, CD2Cl2, δ): 8.80 (m, 1H), 8.10 (m, 1H), 8.04 (m, 1H), 7.57 (m, 3H), 5.18 (s, 2H), 1.43 (s, 12H).

Workup

  1. temperatureThe solution was cooled down in an ice-water bath
  2. additionAfter addition
  3. customto quench
  4. customthe reaction until no gas
  5. customwas produced
  6. customThe solvent was evaporated
  7. extractionthe residue was extracted with ethyl acetate/water

Sources & evidence

ORD record
ord-a5b558da24aa4c308ae3c4da3f5017ea
Source dataset
uspto-grants-2015_01
Patent number
US08937183B2

Reaction notes

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