Methanol → HCID 4102020, compound

HRID 849069Notes

Reaction equation

HRID 849069 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[C:11](OCC)=[O:12])[O:4][CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C.CO.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[CH:11]=[O:12])[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 336004Ethyl 1,4-dioxaspiro[4.5]decane-6-carboxylateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 4102020HCID 4102020, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To the product of Example 74 (10.0 g, 46.7 mmol) in 150 mL of toluene cooled to -78° C. was added dropwise under argon (Ar) 93.5 mL (93.5 mmol) of diisobutylaluminum hydride (DIBAL) in toluene over a 15 min. period. After stirring this reaction for 45 min., MeOH (40 mL) was added dropwise followed by 200 mL of a saturated solution of Rochelle salts (potassium sodium tartrate tetrahydrate). The reaction was warmed to room temperature, stirred for one hour, and the organic layer was separated The aqueous layer was washed with EtOAc and the organic layer was stripped of all toluene. The residue and the EtOAc extract were combined, diluted with EtOAc, washed with water, dried (MgSO4), filtered and stripped of all solvent to yield the crude desired produce. This material was chromatographed through silica gel eluting with a 1:1 mixture of EtOAc and hexane to yield 6.4 g of the title material as a colorless oil.

Workup

  1. customthis reaction for 45 min.
  2. stirringstirred for one hour
  3. customthe organic layer was separated The aqueous layer
  4. washwas washed with EtOAc
  5. extractionThe residue and the EtOAc extract
  6. additiondiluted with EtOAc
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customto yield the crude
  11. customdesired produce
  12. customThis material was chromatographed through silica gel eluting with a 1:1 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-90d35b4b0a1d4dddbc7b2fc7c5191060
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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