5,6-Dihydro-2H-pyran-3-carbaldehyde → 5-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyran

HRID 1011040ノート

反応式

HRID 1011040 の反応式
[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]=1

参加物

5

反応物 3

HCID 834235,6-Dihydro-2H-pyran-3-carbaldehydeHCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromideHCID 178418339Butyllithium

生成物 1

HCID 673137985-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyran収率 41.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  1. customto give a dark orange solution
  2. stirringThe reaction mixture was stirred at room temperature for 20 hours
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give an orange oil
  7. customThe product was purified by silica chromatography
  8. washa gradient elution of 0-25% ethyl acetate/cyclohexane

出典と根拠

ORDレコード
ord-b6ff1ff577a54ff2b20e76af57fc73e6
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

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