Sulfuric Acid → [(1R,2R)-3,3-diethoxy-2-(hydroxymethyl)cyclobutyl]methanol

HRID 2081794노트

반응식

HRID 2081794 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1([O:24][CH2:25][CH3:26])[CH2:13][C@@H:12]([C:14](OCC)=[O:15])[C@@H:11]1[C:19](OCC)=[O:20])[CH3:8].[Cl-].[NH4+].S(=O)(=O)(O)O>C1COCC1.CCOCC>[CH2:25]([O:24][C:10]1([O:9][CH2:7][CH3:8])[CH2:13][C@@H:12]([CH2:14][OH:15])[C@@H:11]1[CH2:19][OH:20])[CH3:26]

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 25517Ammonium ChlorideHCID 14378472trans-3,3-Diethoxy-1,2-cyclobutanedicarboxylic acid, diethyl esterHCID 21226445Aluminium lithium hydride

생성물 1

HCID 14378477[(1R,2R)-3,3-diethoxy-2-(hydroxymethyl)cyclobutyl]methanol수율 70.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of lithium aluminum hydride (2.38 g, 0.0627 mol) in dry THF (50 ml) was added slowly (trans)-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid, diethyl ester (11.29 g, 0.0392 mol) in THF (25 ml) so that a gentle reflux was maintained. The reaction was heated at 55° for 4 hours and then diluted with ether (100 ml) and poured into saturated aqueous ammonium chloride (100 ml). The pH was lowered to 4 with 3M sulfuric acid. The suspension was extracted with ether (4×100 ml) and then chloroform (3×100 ml). The ether extracts were combined, dried over sodium sulfate, filtered and concentrated to give 5.613 g of desired product. The chloroform extracts were combined, dried over sodium sulfate, filtered and concentrated to give 112 mg of additional desired product.

후처리

  1. temperaturea gentle reflux
  2. temperaturewas maintained
  3. temperatureThe reaction was heated at 55° for 4 hours
  4. extractionThe suspension was extracted with ether (4×100 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ec2d61e1a5a40b6b5669ed781a071ba
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05185459

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