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

HRID 1020768Notes

Reaction equation

HRID 1020768 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-9f13664fe78e4cb9a6d6941a5789c0e5
Source dataset
uspto-grants-2014_05
Patent number
US08716475B2

Reaction notes

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