Dimethyl Sulfate → (S)-(+)-2-ethynyl-3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran

HRID 1199248

반응식

HRID 1199248 반응식
[C:1]([C@:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].S(OC)(O[CH3:22])(=O)=O.[OH-].[Na+].[OH-].[NH4+]>CC(C)=O>[C:1]([C@:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([O:15][CH3:22])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2]

참가 물질

6

반응물 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 9859440(S)-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol

생성물 1

HCID 14478580(S)-(+)-2-ethynyl-3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran수율 47%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of (S)-(+)-2-ethynyl-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol (354 mg, 1.54 mmol) in acetone (9 mL) was treated with dimethyl sulfate (0.8 mL), and 50% NaOH (1.2 mL) for 2 h at 25° C. with stirring. Ammonium hydroxide solution (1.0N, 50 mL) was added, and it was extracted with ether (3×50 mL). The extracts were combined, washed with 1.0N HCl, water, and dried over MgSO4. It was filtered and concentrated in vacuo to give 400 mg of solid, which or crystallization from ether-hexane (1:12) afforded 141 mg (47%) of (S)-(+)-2-ethynyl-3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-1-benzopyran as white prisms: mp 94°-97° C., [α]D25 +53.86°, (C 0.4233, CHCl3).

후처리

  1. extractionit was extracted with ether (3×50 mL)
  2. washwashed with 1.0N HCl, water
  3. dry with materialdried over MgSO4
  4. filtrationIt was filtered
  5. concentrationconcentrated in vacuo
  6. customto give
  7. custom400 mg of solid, which or crystallization from ether-hexane (1:12)

출처 및 근거

ORD 기록
ord-364537432f45467080d7564060babd28
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04898962

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