Tetrahydrofuran → HCID 22918667, compound
Reaction equation
BrC[CH2:3][CH:4]1[O:9][CH2:8][CH2:7]C[O:5]1.[Mg].[C:11]([O:14][C:15]1[C:20]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:19][C:18]([O:25][CH3:26])=[C:17]([CH2:27][C:28]([CH3:30])=[O:29])[C:16]=1[C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:13])[CH3:12].[Cl-].[NH4+].O1CCC[CH2:38]1>>[C:11]([O:14][C:15]1[C:20]([C:21]([CH3:24])([CH3:22])[CH3:23])=[CH:19][C:18]([O:25][CH3:26])=[C:17]([CH2:27][C:28]([OH:29])([CH3:38])[CH2:30][CH2:3][CH:4]2[O:5][CH2:7][CH2:8][O:9]2)[C:16]=1[C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:13])[CH3:12]Participants
Procedure
A solution of 2-(2-bromoethyl)-1,3-dioxane (50 g) in tetrahydrofuran (200 ml) was added to magnesium (6.6 g) under a nitrogen atmosphere to prepare a Grignard reagent. A solution of 4-acetoxy-2-acetonyl-3,5-di-tert-butylanisole in tetrahydrofuran (200 ml) was added dropwise to the reagent. After stirring the mixture at room temperature for 3 h, a saturated aqueous solution of ammonium chloride was added and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (33% ethyl acetate in n-hexane) to afford 4-acetoxy-2-[4-(1,3-dioxa-2-cyclopentyl)-2-hydroxy-2-methylbutyl]-3,5-di-tert-butylanisole [27.9 g (yield, 69%)] as a colorless oil.
Workup
- extractionthe resulting mixture was subjected to extraction with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe concentrate was purified by silica gel chromatography (33% ethyl acetate in n-hexane)
Sources & evidence
- ORD record
- ord-5668038139274b01a4a19c480fe6d4a5
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05606089
Reaction notes
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