Toluene → HCID 19353138, compound

HRID 378220Notes

Reaction equation

HRID 378220 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[CH3:18][C:19]1([CH3:37])[CH2:28][CH2:27][C:26]([CH3:30])([CH3:29])[C:25]2[CH:24]=[C:23]([C:31](=[CH2:36])[C:32](OC)=[O:33])[CH:22]=[CH:21][C:20]1=2.C(C(C(C([O-])=O)O)O)([O-])=O.[Na]>ClCCl>[CH3:18][C:19]1([CH3:37])[CH2:28][CH2:27][C:26]([CH3:29])([CH3:30])[C:25]2[CH:24]=[C:23]([C:31](=[CH2:36])[CH2:32][OH:33])[CH:22]=[CH:21][C:20]1=2

Participants

7

Reactant 5

HCID 1140TolueneHCID 38061142,3-DihydroxybutanedioateHCID 5360545SodiumHCID 19353129HCID 19353129, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19353138HCID 19353138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 1M diisobutylaluminium hydride solution in toluene (2.78 ml, 2.78 mmol) is added at 78° C., dropwise, to a solution of methyl 2-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)acrylate (310 mg, 1.14 mmol) in dichloromethane (3 ml). The solution is stirred for 1 h at 0° C., then treated with a solution of double tartrate of sodium [lacuna] and filtered through silica.

Workup

  1. filtrationfiltered through silica

Sources & evidence

ORD record
ord-cd3a3b29d94f4fe5a3f3c5cd6839d6fd
Source dataset
uspto-grants-2000_02
Patent number
US06030952

Reaction notes

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