Diisobutylaluminum hydride → (4-Methyloxan-4-yl)methanol

HRID 2360577Notes

Reaction equation

HRID 2360577 reaction equation
C[O:2][C:3]([C:5]1([CH3:11])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=O.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:11][C:5]1([CH2:3][OH:2])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 9855836Potassium sodium tartarateHCID 11019135Methyl 4-methyloxane-4-carboxylate

Product 1

HCID 59708470(4-Methyloxan-4-yl)methanolYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A −78° C. solution of 4-methyl-tetrahydro-pyran-4-carboxylic acid methyl ester (Regan, J. et al. J. Med. Chem. 2002, 45, 2994-3008; 9.9 g, 63 mmol) in CH2Cl2 (400 mL) was treated with DIBAL-H (1.0 M in CH2Cl2; 125 mL, 125 mmol). The resulting mixture was stirred for 1 h, and then was diluted with EtOAc (200 mL) and satd. aq. NH4Cl. The mixture was treated with satd. aq. sodium potassium tartrate, allowed to warm to rt, and stirred for 45 min. The mixture was extracted with CH2Cl2 (4×), and the combined extracts were washed with satd. aq. NaCl, dried, and concentrated. Chromatography (EtOAc/hexanes) afforded the title compound as a colorless oil (5.6 g 69%). The spectral data matched that reported in PCT Intl. Pat. Appl. Publ. No. WO 2006/001752.

Workup

  1. additionThe mixture was treated with satd
  2. stirringstirred for 45 min
  3. extractionThe mixture was extracted with CH2Cl2 (4×)
  4. washthe combined extracts were washed with satd
  5. dry with materialaq. NaCl, dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dc8e8056a3944420bd353323c2047a7d
Source dataset
uspto-grants-2014_04
Patent number
US08686142B2

Reaction notes

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