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Water → 2-(3-Hydroxymethylthiophen-3-yl)ethanol

HRID 270644
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HRID 270644 반응식
C(C[C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:10]([OH:12])=O)(O)=O.O.[O:14]1CC[CH2:16][CH2:15]1>>[OH:12][CH2:10][C:9]1([CH2:16][CH2:15][OH:14])[CH:8]=[CH:7][S:6][CH2:5]1
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참가 물질

4

반응물 3

HCID 962WaterHCID 8028Tetrahydrofuran3회HCID 206212852-(Carboxymethyl)thiophene-3-carboxylic acid

생성물 1

HCID 693120392-(3-Hydroxymethylthiophen-3-yl)ethanol수율 57%

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온도
-2 °C

실험 절차

0.45 g of the compound obtained in Example 4 was dissolved in 10 mL of anhydrous tetrahydrofuran, and the resulting solution was cooled to −2° C. 3.7 mL of 2M solution of borane-dimethylsulfide complex in tetrahydrofuran was slowly added thereto, and the resulting mixture was allowed to react for at least 1 hour at −1° C. The reaction mixture was warmed to room temperature and further added thereto was 3.7 mL of a 2M solution of borane-dimethylsulfide complex in tetrahydrofuran. The resulting mixture was kept at room temperature for 2 hours, and cooled to 0° C. After adding water thereto, the resulting solution was extracted three times with 15 mL portions of ethyl acetate, and the organic layers were combined, washed with 20 ml of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.22 g (yield of 57%) of the title compound as an oil.

후처리

  1. customto react for at least 1 hour at −1° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. additionfurther added
  4. temperaturecooled to 0° C
  5. extractionthe resulting solution was extracted three times with 15 mL portions of ethyl acetate
  6. washwashed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e9302e4514c54e8d8caa07f7b3178612
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07449580B2

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