Dibenzyl cyclohexane-1,1-dicarboxylate → HCID 18623884, compound

HRID 1860510Notes

Reaction equation

HRID 1860510 reaction equation
[C:1]1([C:17](OCC2C=CC=CC=2)=[O:18])([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH:17]([C:1]1([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:18]

Participants

4

Reactant 2

HCID 15416540Dibenzyl cyclohexane-1,1-dicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18623884HCID 18623884, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dibenzyl cyclohexane-1,1-dicarboxylate (10.5 g, 30 mmol, from Step A) in 100 mL CH2Cl2 was cooled to −78° C. and a solution of diisobutylaluminum hydride (60 mL, 1 M in CH2Cl2, 60 mmol) was added dropwise. After 3.5 h the mixture was carefully quenched with sat'd ammonium chloride and 1 M HCl. The mixture was warmed to rt and poured into 200 mL water and 200 mmL CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over magnesium sulfate and concentrated. Flash chromatography (400 g silica, 10/1 hexane/EtOAc) gave 5.9 g (79%) of the desired aldehyde. 1H NMR (500 MHz, CDCl3) δ1.4-1.6 (m, 16), 1.88-1.95 (m, 2H), 2.03-2.12 (m, 2H), 5.2 (s, 2H), 7.30-7.41 (m, 5H), 9.58 (s, 1H).

Workup

  1. customAfter 3.5 h the mixture was carefully quenched with sat'd ammonium chloride and 1 M HCl
  2. additionpoured into 200 mL water and 200 mmL CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b251ce3f1d63443fb64d943db80be3e6
Source dataset
uspto-grants-2003_03
Patent number
US06531484B2

Reaction notes

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