Aluminium lithium hydride → HCID 57890054, compound

HRID 1819935Notes

Reaction equation

HRID 1819935 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:18]([CH3:37])[CH:17]=2)([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:9]=1[CH3:10])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:33]([Si:30]([CH3:32])([CH3:31])[O:29][CH:24]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:11]([C:7]2[S:6][C:5]([CH2:3][OH:2])=[C:9]([CH3:10])[CH:8]=2)([CH2:12][CH3:13])[CH2:14][CH3:15])=[CH:17][C:18]=1[CH3:37])([CH3:36])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57890161HCID 57890161, compound

Product 1

HCID 57890054HCID 57890054, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 5-(1-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-3,3-dimethyl-butoxy]-3-methyl-phenyl}-1-ethyl-propyl)-3-methyl-thiophene-2-carboxylic acid methyl ester (0.94 g, 1.71 mmol) and THF (50 mL)is added LAH (71 mg, 1.89 mmol). The mixture is stirred for 10 m, warmed to RT and stirred for 2 h. The reaction is quenched with H2O (70 ul), 15% NaOH (70 uL) and H2O (210 uL) and diluted with EtOAc (50 mL). The mixture is filtered through diatomaceous earth and concentrated to give the title compound (0.89 g, 1.72 mmol, 100%). 1H NMR (CDC3), B 0.07 (s, 3H), 0.12 (s, 3H), 0.72 (t, J=7.4 Hz, 6H), 0.91 (s, 9H), 0.98 (s, 9H), 2.01-2.14 (m, 4H), 2.19 (s, 3H), 2.21 (s, 3H), 3.68 (dd, J=5.3, 3.4 Hz, 1H), 3.86 (dd, J=9.0, 5.3 Hz, 1H), 3.98 (dd, J=9.0, 3.4 Hz, 1H), 4.67 (s, 22H), 6.54 (s, 1H), 6.67 (d, J=8.1 Hz, 1H), 7.00-7.06 (m, 2H). LC/MS (m/z): calcd for C30H50O3SSi M+: 518.9; found: 518.0.

Workup

  1. stirringstirred for 2 h
  2. customThe reaction is quenched with H2O (70 ul), 15% NaOH (70 uL) and H2O (210 uL)
  3. additiondiluted with EtOAc (50 mL)
  4. filtrationThe mixture is filtered through diatomaceous earth
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93e4688d638942d4bf3358a05bb41418
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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