Water → (E)-4-[3-Methoxy-4-(methoxymethoxy)phenyl]-3-buten-1-ol

HRID 981139ノート

反応式

HRID 981139 の反応式
C([Li])CCC.[Br-].[OH:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][C:39]=1[O:40][CH2:41][O:42][CH3:43])[CH:35]=O.O>C1COCC1>[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[CH:35]=[CH:10]/[CH2:9][CH2:8][OH:7])[CH:37]=[CH:38][C:39]=1[O:40][CH2:41][O:42][CH3:43]

参加物

6

反応物 4

HCID 962WaterHCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeHCID 11025793Phosphonium, (3-hydroxypropyl)triphenyl-, bromideHCID 178418339Butyllithium

生成物 1

HCID 20071447(E)-4-[3-Methoxy-4-(methoxymethoxy)phenyl]-3-buten-1-ol収率 35.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-Butyllithium (1.6 M in hexane, 25 ml) was added dropwise to a stirred suspension of (3-hydroxypropyl)triphenylphosphonium bromide (8.03 g) in dry THF (50 ml) cooled to 0° under nitrogen. The resulting blood-red solution was stirred at 0° for 10 min and then 3methoxy-4-(methoxymethoxy)benzaldehyde (3.60 g) in dry THF (10 ml) was added dropwise over 5 min. The mixture was allowed to warm to room temperature, stirred for 4 h water (10 ml) was added and the majority of the solvent was removed in vacuo at 40°. A solution of the residual oil in ER (200 ml) was washed with water (150 ml), dried, treated with charcoal, concentrated and purified by [FCS] eluting with EA/hexane (1:1) to give the title compound (1.55 g). T.l.c. (EA-hexane 1:1) Rf 0.30.

後処理

  1. temperaturecooled to 0° under nitrogen
  2. additionwas added
  3. customthe majority of the solvent was removed in vacuo at 40°
  4. washA solution of the residual oil in ER (200 ml) was washed with water (150 ml)
  5. customdried
  6. additiontreated with charcoal
  7. concentrationconcentrated
  8. custompurified by [FCS]
  9. washeluting with EA/hexane (1:1)

出典と根拠

ORDレコード
ord-4aa5abc2b64446508fa58debd6b181ef
出典データセット
uspto-grants-1991_02
特許番号
US04990505

反応ノート

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