Sodium Hydroxide → HCID 59715022, compound

HRID 2223909Notes

Reaction equation

HRID 2223909 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH2:25][CH2:26][C:27]1([CH2:33][CH2:34][O:35][C:36]2[CH:37]=[C:38]([C:45]([O-])=[O:46])[CH:39]=[C:40]([CH:44]=2)[C:41]([O-])=[O:42])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O1CCCC1.O.C(OCC)C>[O:7]([CH2:25][CH2:26][C:27]1([CH2:33][CH2:34][O:35][C:36]2[CH:44]=[C:40]([CH2:41][OH:42])[CH:39]=[C:38]([CH2:45][OH:46])[CH:37]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86760671HCID 86760671, compound

Product 1

HCID 59715022HCID 59715022, compoundYield 83.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (172 mg) was suspended in tetrahydrofuran (10 mL). To this was added a solution of dimethyl 5-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]isophthalate (synthesized in Example 24) (1.30 g) in tetrahydrofuran (15 mL) dropwise at room temperature. The suspension was stirred for 3 hours. Water (0.16 mL) was added to the suspension and it was stirred for 10 minutes. A 15% aqueous sodium hydroxide solution (0.16 mL) was added to the suspension and it was stirred for 15 minutes. Diethyl ether was added to the mixture, followed by addition of water (0.48 mL). The solution was stirred for 30 minutes. The solution was dried over anhydrous magnesium sulfate, filtered and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate] to give the title compound (1.04 g).

Workup

  1. stirringwas stirred for 10 minutes
  2. stirringwas stirred for 15 minutes
  3. stirringThe solution was stirred for 30 minutes
  4. dry with materialThe solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was then concentrated under reduced pressure
  7. customThe resulting residue was purified by chromatography [silica gel, ethyl acetate]

Sources & evidence

ORD record
ord-229f3a31a1f94a73811a543dc0e0e36a
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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