Disodium 2,3-dihydroxybutanedioate → HCID 19741712, compound

HRID 2255125Notes

Reaction equation

HRID 2255125 reaction equation
[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[H-].C([Al+]CC(C)C)C(C)C.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1COCC1.C(OCC)C>[Br:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5462222PotassiumHCID 19741700HCID 19741700, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19741712HCID 19741712, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of methyl 4-(bromomethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzoate (1.59 g, 4.2 mmol) from Preparation 14 in THF 15 mL), cooled to -78° C. is treated with diisobutylaluminum hydride (1M, 10.4 mL, 10.4 mmol). The reaction mixture is stirred for 3.5 hours. The reaction mixture is treated with 20 mL of a saturated potassium-, sodium-tartrate solution, diethylether (200 mL) and is allowed to warm to room temperature. The organic phase is separated, dried (MgSO4), and concentrated. The residue is purified by silica gel chromatography (1% MeOH/CH2Cl2). An oil of 4-(bromomethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzenemethanol is obtained (1.02 g, 74%).

Workup

  1. temperatureto warm to room temperature
  2. customThe organic phase is separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-acd1d38974cc44669f508a825e6f61db
Source dataset
uspto-grants-1993_08
Patent number
US05238958

Reaction notes

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