Acetone → HCID 86737362, compound

HRID 1732270Notes

Reaction equation

HRID 1732270 reaction equation
C[C:2](C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]1([CH2:26][CH2:27][CH2:28][CH:29]([CH3:38])[CH2:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH:21]2[O:22][C:18]([CH2:23][CH:24]=[O:25])([CH2:19][CH2:20]2)[CH2:17][O:16]1.CC(C)=O.[N+](=C)=[N-]>CCOCC.O.C(OCC)(=O)C.CC(O)C>[CH3:14][C:15]1([CH2:26][CH2:27][CH2:28][CH:29]([CH3:38])[CH2:30][O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH:21]2[O:22][C:18]([CH2:23][C:24]([O:3][CH3:2])=[O:25])([CH2:19][CH2:20]2)[CH2:17][O:16]1

Participants

9

Reactant 4

HCID 180AcetoneHCID 9550DiazomethaneHCID 86737361HCID 86737361, compoundHCID 131709961Jones' reagent

Product 1

HCID 86737362HCID 86737362, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

An excess of Jones reagent (4 ml, 4 mM) is added slowly to a mixture of (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetaldehyde (813 mg, 2.3 mM) and acetone (20 ml) at 0° C. The resulting mixture is stirred for thirty minutes and treated with 2-propanol (2 ml) followed by ethyl acetate (50 ml) and water (20 ml). The organic layer is separated and the aqueous layer is extracted with ethyl acetate (3×20 ml). The combined organic layers are dried (sodium sulfate) and the solvent is removed in vacuo to give a pale yellow oil. The oil is redissolved in ether (15 ml), treated with an excess of diazomethane in ether and stirred for ten minutes. The solvent is removed in vacuo to give methyl (1RS,4SR,5RS)-4-methyl-4-[4-methyl-5-(tetrahydropyran-2-yloxy)pentyl]-3,8-dioxabicyclo [3.2.1] octane-1-acetate as a pale yellow oil (625 mg, 83%). This material is homogeneous by thin layer chromatography and is used directly in the next step.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organic layers are dried (sodium sulfate)
  4. customthe solvent is removed in vacuo
  5. customto give a pale yellow oil
  6. stirringstirred for ten minutes
  7. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-5f0e8de4cdef484daa2286b6a180bec1
Source dataset
uspto-grants-1980_12
Patent number
US04237054

Reaction notes

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