Potassium sodium tartarate → HCID 22641091, compound

HRID 2305614Notes

Reaction equation

HRID 2305614 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:37])[CH2:21][CH2:20][C:19]([CH3:23])([CH3:22])[C:18]2[CH:17]=[C:16]([Se:24][C:25]#[C:26][C:27]3[CH:36]=[CH:35][C:30]([C:31](OC)=[O:32])=[CH:29][CH:28]=3)[CH:15]=[CH:14][C:13]1=2.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[CH3:11][C:12]1([CH3:37])[CH2:21][CH2:20][C:19]([CH3:22])([CH3:23])[C:18]2[CH:17]=[C:16]([Se:24][C:25]#[C:26][C:27]3[CH:36]=[CH:35][C:30]([CH2:31][OH:32])=[CH:29][CH:28]=3)[CH:15]=[CH:14][C:13]1=2

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 22641073HCID 22641073, compound

Product 1

HCID 22641091HCID 22641091, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1 M solution of diisobutylaluminium hydride in toluene (4 ml, 4 mmol) is added dropwise, at 0° C., to a solution of methyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)benzoate obtained according to Example 4 (750 mg, 1.8 mmol), in toluene (20 ml). The solution is stirred for 4 h at 0° C. and is then treated with a double potassium sodium tartrate solution, filtered and taken up in a mixture of ethyl ether and water. The organic phase is washed with water, dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. 418 mg (60%) of a colourless oil are obtained.

Workup

  1. customobtained
  2. filtrationfiltered
  3. additiontaken up in a mixture of ethyl ether and water
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated on a rotary evaporator under vacuum at 40° C

Sources & evidence

ORD record
ord-a194492c583c477b8142b815580f3389
Source dataset
uspto-grants-2002_08
Patent number
US06441010B2

Reaction notes

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