Water → HCID 11992771, compound

HRID 2241057Notes

Reaction equation

HRID 2241057 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][C:3]=1[O:25][CH2:26][C:27](OCC)=[O:28].CC(C[AlH]CC(C)C)C.O>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][C:3]=1[O:25][CH2:26][CH2:27][OH:28]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 86621473HCID 86621473, compound

Product 1

HCID 11992771HCID 11992771, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 42 (93 mg, 0.22 mmol) was dissolved in THF (5 mL) and cooled to 0° C. under nitrogen. DIBAL-H (1M in hexane, 370 μL, 0.55 mmol) was added drop-wise over several minutes. The ice bath was removed and the stirring reaction allowed to warm to ambient temperature. The reaction was re-cooled to 0° C. and water (10 mL) added dropwise over several minutes. The ice bath was removed and the reaction stirred until solids began to form. The solids were filtered and the filtrate washed several time with dichloromethane to ensure all product was removed from the aluminate solids. The filtrate was concentrated in vacuuo to give 82 mg (98%) of compound 44 as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.88 (s, 6H), 0.91 (s, 6H), 1.25 (s, 2H), 1.77 (s, 2H), 1.90 (s, 2H), 2.20 (s, 3H), 3.91-3.98 (m, 2H), 4.02-4.15 (m, 2H), 6.68 (d, J=8.1 Hz, 1H) 6.75-7.05 (m, 2H), 7.09-7.15 (m, 3H) 7.25-7.36 (m, 2H).

Workup

  1. customThe ice bath was removed
  2. customthe stirring reaction
  3. temperatureto warm to ambient temperature
  4. temperatureThe reaction was re-cooled to 0° C.
  5. customThe ice bath was removed
  6. customto form
  7. filtrationThe solids were filtered
  8. washthe filtrate washed several time with dichloromethane
  9. customwas removed from the aluminate solids
  10. concentrationThe filtrate was concentrated in vacuuo

Sources & evidence

ORD record
ord-4b6d9543231644bb8594252a2278ff86
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

Loading…