5,6-Dihydro-2H-pyran-3-carbaldehyde → HCID 67313798, compound
Reaction equation
[Br-].[CH2:2]([O:9][CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[O:37]1[CH2:42][CH2:41][CH:40]=[C:39]([CH:43]=O)[CH2:38]1>O1CCCC1>[C:3]1([CH2:2][O:9][CH2:10][CH2:11][CH:12]=[CH:43][C:39]2[CH2:38][O:37][CH2:42][CH2:41][CH:40]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of (3-benzyloxypropyl)triphenylphosphonium bromide (9.90 g) in dry tetrahydrofuran (30.5 ml) at −15° C. was added butyllithium (8.06 ml, 2.5M in hexanes) dropwise to give a dark orange solution. The reaction temperature was increased to 0° C. and stirring was continued for 30 minutes. A solution of 5,6-dihydro-2H-pyran-3-carbaldehyde (2.26 g) in dry tetrahydrofuran (3 ml) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was filtered through celite and washed with diethyl ether. The filtrate was concentrated in vacuo to give an orange oil. The product was purified by silica chromatography using a gradient elution of 0-25% ethyl acetate/cyclohexane to afford the title compound as a colourless oil (2.04 g).
Workup
- customto give a dark orange solution
- stirringThe reaction mixture was stirred at room temperature for 20 hours
- filtrationThe reaction mixture was filtered through celite
- washwashed with diethyl ether
- concentrationThe filtrate was concentrated in vacuo
- customto give an orange oil
- customThe product was purified by silica chromatography
- washa gradient elution of 0-25% ethyl acetate/cyclohexane
Sources & evidence
- ORD record
- ord-b6ff1ff577a54ff2b20e76af57fc73e6
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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