Water → HCID 11137304, compound

HRID 1009805Notes

Reaction equation

HRID 1009805 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([C:7](OC)=[O:8])[C@@H:4]([CH3:11])[O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.CCOC(C)=O.O>C(Cl)Cl>[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH3:11])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 6544468(4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylateHCID 68718528lithium aluminium hydride THF

Product 1

HCID 11137304HCID 11137304, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of commercial (4S,5R)-methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (2.5 g, 14.4 mmol) in CH2Cl2 (50 ml) at 0° C. was added 1M LiAlH4/THF (35.9 ml, 35.9 mmol). After stirring overnight at RT and cooling to 0° C., EtOAc (5.0 mL) was added. Stirring was continued at RT for 30 min prior to addition of water (50 mL); whereupon, the aqueous mixture was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with sat'd NaCl, dried (Na2SO4), and concentrated. Chromatography (SiO2 230-400 mesh, Hex to 85/15 Hex/EtOAc) of the crude product afforded the expected alcohol (1.18 g, 56% yield) as a clear liquid: 1H NMR δ (CDCl3) 4.02 (m, 1H), 3.81 (dd, J=12.1, 2.8 Hz, 1H), 3.65 (m, 1H), 3.60 (dd, J=12.1, 4.4 Hz, 1H), 1.43 (s, 1H), 1.40 (s, 3H), 1.29 (d, J=6.1 Hz, 3H).

Workup

  1. temperaturecooling to 0° C.
  2. stirringStirring
  3. waitwas continued at RT for 30 min
  4. extractionwhereupon, the aqueous mixture was extracted with EtOAc (2×100 mL)
  5. washThe combined organic extracts were washed with sat'd NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e97017b0fa0d410db2d659ddfcdd12eb
Source dataset
uspto-grants-2011_07
Patent number
US07973159B2

Reaction notes

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