Trimethyl borate → 2-(3-Hydroxymethylthiophen-2-yl)ethanol

HRID 270642

반응식

HRID 270642 반응식
B.[Na].[Br-].[Li+].B(OC)(OC)OC.C[O:13][C:14]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1[C:22](OC)=[O:23])=O>O1CCCC1.O.C(OCC)C.CO>[OH:23][CH2:22][C:21]1[CH:20]=[CH:19][S:18][C:17]=1[CH2:16][CH2:14][OH:13]

참가 물질

9

반응물 4

HCID 8470Trimethyl borateHCID 82050Lithium BromideHCID 58952963Methyl 2-(2-methoxy-2-oxoethyl)thiophene-3-carboxylateHCID 178418435HCID 178418435, 화합물

생성물 1

HCID 111827612-(3-Hydroxymethylthiophen-2-yl)ethanol수율 90.6%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To 800 mL of anhydrous tetrahydrofuran, 31.0 g of sodium boron hydride and 71.3 g of lithium bromide were added, and then 10.6 mL of trimethyl borate was added thereto dropwise at 0° C. The resulting mixture was stirred at room temperature for 30 minutes, and then a solution obtained by dissolving 70.4 g of the compound obtained in Example 1 in 200 mL of tetrahydrofuran was slowly added over 2 hours while allowing the resulting mixture to reflux. The reaction solution was further refluxed for 2 hours then cooled to room temperature. 100 mL of anhydrous methanol was added slowly to the solution, and then 700 mL of ethyl ether and 700 mL of water were added. The organic phase was collected, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 47.1 g (yield of 90%) of the title compound as an oil.

후처리

  1. customdropwise at 0° C
  2. customa solution obtained
  3. additionwas slowly added over 2 hours
  4. temperatureto reflux
  5. temperatureThe reaction solution was further refluxed for 2 hours
  6. temperaturethen cooled to room temperature
  7. customThe organic phase was collected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-da60a17647834b40847d67500597ec76
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449580B2

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