Water → HCID 20071447、化合物

HRID 568879

反応式

HRID 568879 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 20071447HCID 20071447、化合物収率 35.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-Butyllithium (1.6M 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 3-methoxy-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 FCC eluting with EA-H (1:1) to give the title compound (1.55 g). T.l.c. (EA-H 1:1) Rf 0.30.

後処理

  1. temperaturecooled to 0° under nitrogen
  2. stirringstirred for 4 h
  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 FCC
  9. washeluting with EA-H (1:1)

出典と根拠

ORDレコード
ord-6969517f20b34f40ad438433119293c4
出典データセット
uspto-grants-1988_03
特許番号
US04730008

関連ノート

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