Water → HCID 11992774, compound

HRID 2241059Notes

Reaction equation

HRID 2241059 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][CH2:27][CH2:28][C:29](O)=[O:30].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][CH2:28][CH2:29][OH:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 11992773HCID 11992773, compound

Product 1

HCID 11992774HCID 11992774, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Compound 47 (50 mg, 0.11 mmol) was dissolved in THF (5 mL) and cooled to 0° C. under nitrogen. DIBAL (1.5 M in hexane, 500 ul, 0.33 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 then cooled back to 0° C. and water (10 mL) added dropwise over several minutes. The ice bath was then removed and the reaction was stirred until solids began to form. The solids were filtered and the filtrate washed several times with dichloromethane. The filtrate was concentrated in vacuuo to give 42 mg (98%) of compound 48 as a clear oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (s, 6H), 0.95 (s, 6H), 1.29 (s, 2H), 1.75 (s, 2H), 1.90 (s, 2H), 2.08-2.17 (m, 5H), 2.55 (t, J=7.3 Hz, 2H), 3.72 (t, J=6.3 Hz, 2H), 3.97 (t, J=6.1 Hz, 2H), 6.70 (d, J=9.0 Hz, 1H), 6.91-6.99 (m, 2H), 7.10-7.20 (m, 3H), 7.20-7.30 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-7416da88a4254833b942619f4f1f02af
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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