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Methanol → 3a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

HRID 2358274
Notes
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Reaction equation

HRID 2358274 reaction equation
C[O-].[Na+].CO.[CH3:6][C:7]12[C:15](=[O:16])[CH2:14][CH2:13][CH:12]1[CH:11]([O:17][CH2:18][C:19](=[O:29])[CH2:20][CH2:21][CH2:22][C:23]1([CH3:28])[O:27][CH2:26][CH2:25][O:24]1)[C:10](=O)[CH2:9][CH2:8]2>C1(C)C=CC=CC=1>[CH3:6][C:7]12[C:15](=[O:16])[CH2:14][CH2:13][CH:12]1[CH:11]1[C:10]([CH2:9][CH2:8]2)=[C:20]([CH2:21][CH2:22][C:23]2([CH3:28])[O:27][CH2:26][CH2:25][O:24]2)[C:19](=[O:29])[CH2:18][O:17]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 684608567a-Methyl-4-[5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-pentyloxy]-hexahydro-indene-1,5-dione

Product 1

HCID 684591043a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
0 °C

Procedure

A 25% (w/w) solution of sodium methoxide in methanol (2.71 mL, 12.8 mmol, 1 eq) was added to the stirred solution of 7a-Methyl-4-[5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-pentyloxy]-hexahydro-indene-1,5-dione (4.5 g, 12.8 mmol, 1 eq) in toluene (200 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then the reaction was quenched with a 10:1 (v/v) of ammonium chloride/potassium bisulfate solution (100 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL), and the combined organic layer was dried with magnesium sulfate. The resulting solution was then filtered and concentrated to yield the title compound as an oil, which was used in the next step without further purification.

Workup

  1. customthe reaction was quenched with a 10:1 (v/v) of ammonium chloride/potassium bisulfate solution (100 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe combined organic layer was dried with magnesium sulfate
  4. filtrationThe resulting solution was then filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-93cac694a7e04e3b8f88cb9ce2d4fbbb
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07763648B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes