Ammonia → 3-Mercapto-3-methylhexan-1-ol

HRID 397243노트

반응식

HRID 397243 반응식
C([S:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12])C1C=CC=CC=1.N.CCO.Cl>CCOCC>[SH:8][C:9]([CH3:16])([CH2:13][CH2:14][CH3:15])[CH2:10][CH2:11][OH:12]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 22648514HCID 22648514, 화합물

생성물 1

HCID 101300393-Mercapto-3-methylhexan-1-ol수율 112.6%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

At a temperature of −78° C. to a solution of 16.0 g (67.1 mmol) of (rac)-3-benzylsulfanyl-3-methyl-hexan-1-ol of step (c) in 200 ml of Et2O was added from a cylinder about 200 ml of NH3 Then pieces of Na (ca. 4.0 g) were added until the reaction mixture remained blue for more than 20 min. The blue colored mixture was allowed to warm up to room temperature overnight and EtOH was added until the blue color disappeared. The mixture was then acidified with about 2.7 M of HCl, and extracted three times with 150 ml of Et2O. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. Distillation of the crude product at reduced pressure (40 mbar/130° C.) gave 11.2 g (73%) of (rac)-3-mercapto-3-methyl-hexan-1-ol in form of a colorless oil.

후처리

  1. waitremained blue for more than 20 min
  2. extractionextracted three times with 150 ml of Et2O
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. distillationDistillation of the crude product at reduced pressure (40 mbar/130° C.)

출처 및 근거

ORD 기록
ord-f2e28fcbbb3a42f5b4cd0c40e494d7f1
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610346B1

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