Diisobutylaluminum hydride → HCID 11176741, compound

HRID 2252474Notes

Reaction equation

HRID 2252474 reaction equation
CC(C[AlH]CC(C)C)C.[Si:10]([O:17][C@@H:18]([CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C@H:19]([CH3:27])/[CH:20]=[CH:21]/[C:22](OCC)=[O:23])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>C(Cl)Cl>[Si:10]([O:17][C@@H:18]([CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:32])[CH3:33])[C@H:19]([CH3:27])/[CH:20]=[CH:21]/[CH2:22][OH:23])([C:13]([CH3:14])([CH3:15])[CH3:16])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 11373806HCID 11373806, compound

Product 1

HCID 11176741HCID 11176741, compoundYield 96,907.797%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIBAL-H (26.5 mL, 26.5 mmol, 1.0 M solution in hexane) was added to the ester 10 (3.14 g. 7.30 μmol) in CH2Cl2 (35 mL) at −78° C. dropwise and stirred for 1 h. The reaction mixture was quenched by EtOAc (5 mL) and sat'd sodium potassium tartrate solution (20 mL) followed by vigorous stirring for 4 h. The aqueous phase was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were washed with brine (10 mL). After drying over MgSO4 and evaporation under vacuum, flash column chromatography (hexane/EtOAc 4:1) provided 2.75 g of alcohol 11 (97%) as a colorless oil: IR (CHCl3) 3349, 2956, 2928, 2857, 1471, 1462, 1255, 1099, 836, 774 cm−1; 1H NMR (300 MHz, CDCl3) ε5.57 (m, 2H), 4.03 (m, 2H), 3.70 (ddd, J=9.7, 6.0, 3.8 Hz, 1H), 3.59 (m, 2H), 2.27 (m, 1H), 2.00 (s, 1H), 1.53 (q, J=6.5 Hz, 2H), 0.96 (d, J=6.9 Hz, 3H), 0.85 (s, 9H), 0.84 (s, 9H), 0.00 (m, 12H); 13C NMR (75 MHz, CDCl3) δ 134.7, 129.2, 72.4, 63.6, 60.1, 41.8, 36.3, 25.9, 18.2, 18.0, 15.1, 10.7, −4.6, −5.4; LRMS (EI) 370 (M−H2O), 303, 171, 147; HRMS (EI) calcd for C20H42O2Si2 370.2723 (M−H2O), found 370.2725; [α]20D−3.0 (c 0.57, CHCl3).

Workup

  1. customThe reaction mixture was quenched by EtOAc (5 mL)
  2. stirringby vigorous stirring for 4 h
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×30 mL)
  4. washthe combined organic layers were washed with brine (10 mL)
  5. dry with materialAfter drying over MgSO4 and evaporation under vacuum, flash column chromatography (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-8c1f59849e424f21aaf16e390a093e61
Source dataset
uspto-grants-2008_01
Patent number
US07321046B2

Reaction notes

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