Methanol → 1,4-Dioxaspiro(4.5)decane-8-carbaldehyde
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.CC(C[AlH]CC(C)C)C.CO.[Cl-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:10]1[C:9]2([CH2:14][CH2:15][CH:6]([CH:4]=[O:3])[CH2:7][CH2:8]2)[O:13][CH2:12][CH2:11]1Participants
7
Procedure
A solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (5.4 g, 25.2 mmol, prepared as in STEP A above) in anhydrous toluene (25 mL) was cooled to −78° C. under an argon atmosphere. To the resulting solution was added a solution of DIBAL-H (26 mL, 1N DIBAL-H in toluene, 26 mmol) in toluene while ensuring the inside temperature was kept between −60 to −70° C. Methanol (25 mL) was added slowly and the resulting mixture was allowed to warm to room temperature, then treated with aqueous sodium chloride (20 mL). The resulting mixture was passed through a silica gel plug (100 g) using ethyl acetate. The resulting eluent was concentrated to yield 1,4-dioxa-spiro[4.5]decane-8-carbaldehyde.
Workup
- customwas kept between −60 to −70° C
- concentrationThe resulting eluent was concentrated
Sources & evidence
- ORD record
- ord-e527984f0c6b4036a9fee9ba1e24ae51
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08217060B2
Reaction notes
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