Sodium Chloride → 1,4-Bis(4-methoxybenzyloxy)butan-2-ol

HRID 1089256

반응식

HRID 1089256 반응식
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][CH2:9][CH:10]=[CH:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[OH-:25].[Na+].[BH4-].[Na+].[Cl-].[Na+]>O1CCCC1.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][O:13][CH2:12][CH:11]([OH:25])[CH2:10][CH2:9][O:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=2)=[CH:20][CH:19]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 545551371,4-Bis(4-methoxybenzyloxy)but-2-ene

생성물 1

HCID 148142131,4-Bis(4-methoxybenzyloxy)butan-2-ol수율 91%

시약·촉매·용매 2

HCID 2723924Mercury bis(trifluoroacetate)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of mercury (II) trifluoroacetate (17.1 g, 40 ml) in aqueous tetrahydrofuran (1:1, 80 ml) was added a solution of 1,4-bis(4-methoxybenzyloxy)but-2-ene (12.8 g, 39 mmol) in tetrahydrofuran (10 ml) over 5 minutes. The resulting 2-phase mixture was stirred vigorously at room temperature for 15 minutes. To the mixture was added aqueous sodium hydroxide (40 ml, 3M) followed by sodium borohydride (0.5M solution in 3M sodium hydroxide; 40 ml) with water-bath cooling. The solution was saturated with sodium chloride and allowed to stand. The organic layer was collected, dried (magnesium sulphate) and filtered through celite. The solvent was removed to afford 1,4-bis(4-methoxybenzyloxy)butan-2-ol (12.27 g, 91%), IR: υmax (KBr) 3440, 2940, 2860, 1610, 1510 and 1250 cm-1 ; 1H NMR: δH (CDCl3) 1.76 (2H, q, J=6.0 Hz, 3-H), 2.90 (1H, br, D2O exchangeable, OH), 3.41 (2H, AB of ABX JAX =6.9 Hz, JBX =4.2 Hz and JAB =9.5 Hz, 1-H), 3.62 (2H, m, 4-H), 3.80 (6H, s, 2×CH3), 4.00 (1H, m, 2-H), 4.43 (2H, s, ArCH2), 4.48 (2H, s, ArCH2), 6.86 (4H, m, ArH) and 7.24 (4H, m, ArH).

후처리

  1. temperaturecooling
  2. customThe organic layer was collected
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered through celite
  5. customThe solvent was removed

출처 및 근거

ORD 기록
ord-877aa27bbb244298bdf0934a84ff7f98
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04965270

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