Diisobutylaluminum hydride → HCID 22181673, compound

HRID 1796332Notes

Reaction equation

HRID 1796332 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[C:14]([Cl:20])=[N:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.CC(C[AlH]CC(C)C)C>CCOCC>[Cl:20][C:14]1[C:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=2)(=[O:11])=[O:12])=[CH:18][CH:17]=[C:16]([CH3:19])[N:15]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86005583HCID 86005583, compound

Product 1

HCID 22181673HCID 22181673, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

4-(2-Chloro-6-methylpyridine-3-sulfonyl)-benzoic acid methyl ester, synthesized following the procedure of Example 9 parts A–D in 39% overall yield, (1.29 g, 3.96 mmol) was dissolved in 25 mL of dry ether and cooled to −78° C. To that a 1 M solution of DIBAL-H in hexanes (8.71 mL, 8.71 mmol) was added and the reaction mixture was allowed to warm to 25° C. and stirred for 4 h. The reaction was quenched with water followed by 1 N HCl (40 mL), stirred for 15 min, neutralized with 50% NaOH and extracted with ether and the ether extracts were combined, washed with brine, dried and stripped in vacuo to give 1.15 g of [4-(2-chloro-6-methylpyridine-3-sulfonyl)-phenyl]-methanol.

Workup

  1. temperatureto warm to 25° C.
  2. customThe reaction was quenched with water
  3. stirringstirred for 15 min
  4. extractionextracted with ether
  5. washwashed with brine
  6. customdried

Sources & evidence

ORD record
ord-6971a613bfd54f67bf7ee0e9f5cc7967
Source dataset
uspto-grants-2006_04
Patent number
US07030145B2

Reaction notes

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