Aluminium lithium hydride → HCID 68503107, compound

HRID 1295544Notes

Reaction equation

HRID 1295544 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([O:35][CH2:36][CH2:37][CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[C:22]=1[O:23][CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:16](OC)=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([O:35][CH2:36][CH2:37][CH2:38][O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[C:22]=1[O:23][CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29])[CH2:16][OH:17])([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68504527HCID 68504527, compound

Product 1

HCID 68503107HCID 68503107, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ester 10 (13.0 g, 18.5 mmol) and LiAlH4 (0.77 g, 20 mmol) in anhydrous THF (100 mL) were stirred at 0° C. for 1 hour. The reaction was quenched by the slow addition of H2O (20 mL). The reaction mixture was concentrated to approximately half volume and was then partitioned between EtOAc (250 mL) and water (500 mL). The aqueous phase was extracted with additional EtOAc (2×100 mL). The combined organic layers were dried over MgSO4 and concentrated to yield 10.82 g (87%) of 11 as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 6.56 (s, 2H), 4.58 (d, 2H, J=4.5 Hz), 3.99-4.07 (m, 6H), 3.76-3.82 (m, 6H), 1.98 (quint, 4H, J=6.0 Hz), 1.91 (quint, 2H, J=6.0 Hz), 0.87 (s, 18H), 0.86 (s, 9H), 0.03 (s, 12H), 0.02 (s, 6H); 13C NMR (75 MHz, CDCl3), δ 152.9, 136.9, 136.3, 104.9, 70.3, 65.4, 65.2, 60.3, 59.6, 33.5, 32.5, 25.8, 18.2, −5.4, −5.5; IR (film, NaCl) 3435 cm−1 (broad); High Resolution MS (electrospray), m/z 695.4178 (Calcd for C34H68O7Si3+Na+: 695.4171).

Workup

  1. customThe reaction was quenched by the slow addition of H2O (20 mL)
  2. concentrationThe reaction mixture was concentrated to approximately half volume
  3. customwas then partitioned between EtOAc (250 mL) and water (500 mL)
  4. extractionThe aqueous phase was extracted with additional EtOAc (2×100 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0cf1fc00535b4910917552c13b1007df
Source dataset
uspto-grants-2007_07
Patent number
US07244295B2

Reaction notes

Loading…