HCID 22221627, compound → HCID 10286021, compound

HRID 1835985Notes

Reaction equation

HRID 1835985 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:18](O)=[O:19])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1>C1COCC1>[OH:19][CH2:18][C:4]1[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=[C:2]([OH:1])[CH:3]=1

Participants

3

Reactant 1

HCID 22221627HCID 22221627, compound

Product 1

HCID 10286021HCID 10286021, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Acid 24 (0.030 g, 0.112 mmole) in 5 mL THF was added a solution of Borane-THF complex (2.0 mL, 2.0 mmole) in THF. After stirring at 65° C. for 6 hours, the THF was evaporated and the residue was poured into 2N HCl and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was separated by HPLC (70:30, H2O/AcCN) to afford 0.011 g (36%) of benzyl alcohol 25 as a white solid: Mp=258-260° C.; 1H NMR (DMSO-d6) δ 9.81 (s, 1 H), 9.45 (s, 1 H), 7.70 (d, 2 H, J=8.9 Hz), 7.00 (s, 1 H), 6.86 (d, 2 H, J=8.7 Hz), 6.76 (s, 2H), 5.27 (m, 1 H), 4.75 (d, 2 H, J=5.6 Hz); MS 255 (M−H)−

Workup

  1. customthe THF was evaporated
  2. additionthe residue was poured into 2N HCl
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe organic phases were concentrated
  7. customthe residue was separated by HPLC (70:30, H2O/AcCN)

Sources & evidence

ORD record
ord-e01c916e37a0470daa1664f3be427497
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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