Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate → 1,4-Dioxaspiro[4.5]decan-8-ylmethanol
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[O:10]1[C:9]2([CH2:14][CH2:15][CH:6]([CH2:4][OH:3])[CH2:7][CH2:8]2)[O:13][CH2:12][CH2:11]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (2.00 g, 9.33 mmol) in tetrahydrofuran (40 mL) at 0° C. was treated dropwise with a 1.0M solution of lithium aluminum hydride in tetrahydrofuran (10.0 mL, 10.0 mmol). The reaction mixture was stirred at 0° C. for 30 min and was then quenched by the dropwise addition of ethyl acetate. The reaction was then diluted with a saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate 3×25 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure (1,4-dioxa-spiro[4.5]dec-8-yl)-methanol (1.60 g, 99.9%) as a colorless oil.
Workup
- customwas then quenched by the dropwise addition of ethyl acetate
- additionThe reaction was then diluted with a saturated aqueous ammonium chloride solution (25 mL)
- extractionextracted with ethyl acetate 3×25 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b231ff6c686d42eaaacc6de039b4fef6
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259166B2
Reaction notes
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