Triphenylphosphine → Phosphonium, [3-(methoxymethoxy)propyl]triphenyl-, bromide

HRID 491339

反応式

HRID 491339 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH3:8].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:8][O:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 127092881-Bromo-3-methoxymethoxypropane

生成物 1

HCID 11178287Phosphonium, [3-(methoxymethoxy)propyl]triphenyl-, bromide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 1-bromo-3-(methoxymethoxy)propane (0.46 g, 2.5 mmol) in anhydrous toluene (1.5 mL) was added triphenylphoshine (0.71 g, 2.7 mmol) under argon with stirring. The mixture was heated at 100° C. for 20 h and cooled to room temperature. The liquid was decanted and the solid residue was grounded with spatula, filtered and washed several times with ether. After drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%) could be used in the Wittig reaction without further purification. A: 1H NMR (500 MHz, CDCl3) δ 1.96 (2H, m, CH2—CH2—CH2), 3.31 (3H, s, O—CH3), 3.85 (2H, br t, J=5.6 Hz, CH2—CH2—O), 4.00 (2H, m, P—CH2), 4.60 (2H, s, O—CH2—O), 7.70, 7.79 and 7.86 (6H, 3H and 6H, each m, Ar—H); Anal. Calcd for C23H26O2PBr: C, 62.03, H, 5.88, Br, 17.94. Found: C, 61.87, H, 5.77, Br, 17.89.

後処理

  1. temperaturecooled to room temperature
  2. customThe liquid was decanted
  3. filtrationfiltered
  4. washwashed several times with ether
  5. dry with materialAfter drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%)
  6. customcould be used in the Wittig reaction without further purification

出典と根拠

ORDレコード
ord-e750918d95f54791b57ec57a9dc3a01c
出典データセット
uspto-grants-2009_05
特許番号
US07531527B2

関連ノート

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