Methanol → 2-(4-Chlorobutyl)-1,3-dithiane-2-carboxylic acid

HRID 1803200

반응식

HRID 1803200 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:12]([O:14]CC)=[O:13])[S:11][CH2:10][CH2:9][CH2:8][S:7]1.[Li+].[OH-].CO>C1COCC1.O>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:12]([OH:14])=[O:13])[S:7][CH2:8][CH2:9][CH2:10][S:11]1

참가 물질

6

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86649922Ethyl 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylate

생성물 1

HCID 581100162-(4-Chlorobutyl)-1,3-dithiane-2-carboxylic acid수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Step AS (2): To a solution of ethyl 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylate (550 mg, 1.94 mmol) in THF (5 mL) was added a solution of LiOH (233 mg, 9.72 mmol) in water (2 mL). Methanol (2 mL) was added and the resulting mixture was stirred at rt for 2 d. The solvents were removed in vacuo. Aqueous 1 N HCl (50 mL) was added. The mixture was extracted with EtOAc (80 mL). The organic layer was washed with water, dried over sodium sulfate, filter, and concentrated in vacuo to afford 2-(4-chlorobutyl)-1,3-dithiane-2-carboxylic acid (400 mg, 1.57 mmol, 81% yield). LC-MS (M+H)+ 253.0. The crude product was used for subsequent chemistry without purification.

후처리

  1. customThe solvents were removed in vacuo
  2. additionAqueous 1 N HCl (50 mL) was added
  3. extractionThe mixture was extracted with EtOAc (80 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-203d55182dac483797d0336629fe16b8
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349880B2

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