Sulfuric Acid → (4S)-4-(2-tetrahydropyranyloxy)-2-nonynal

HRID 973339노트

반응식

HRID 973339 반응식
[OH:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]#[C:4][CH:5]=[O:6].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.S(=O)(=O)(O)O>O.CCOCC>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C@@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]#[C:4][CH:5]=[O:6]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 86735171(4S)-4-hydroxy-2-nonynal

생성물 1

HCID 86735172(4S)-4-(2-tetrahydropyranyloxy)-2-nonynal

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of (4S)-4-hydroxy-2-nonynal (41.6 g., 0.27 mole) and dihydropyran (33.6 g., 0.4 mole) is cooled to 5° by means of an ice bath and is treated with 0.2 mole of concentrated sulfuric acid. This is allowed to warm to room temperature and stand 17 hours. It is then diluted with water. The oily product is taken up in ether, washed with sodium bicarbonate solution and water and dried over sodium sulfate. Distillation affords (4S)-4-(2-tetrahydropyranyloxy)-2-nonynal as a colorless oil.

후처리

  1. temperatureis cooled to 5° by means of an ice bath
  2. washwashed with sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. distillationDistillation

출처 및 근거

ORD 기록
ord-4b333c9749534a9cbe1332309c788255
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04055597

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