Ethanol → HCID 11790021, compound

HRID 1416360Notes

Reaction equation

HRID 1416360 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2.[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:14]=1.C(O)C.O1CCCC1>ClCCl>[CH2:13]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2)[CH3:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 13422906HCID 13422906, compound

Product 1

HCID 11790021HCID 11790021, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 5-hydroxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.5 g, 3.07 mmol), triphenylphosphine (1.0 g, 3.83 mmol) and ethanol (0.27 mL, 4.61 mmol) in dry tetrahydrofurane 0.597 mL (3.83 mmol) diethyldiazodicarboxylate was added dropwise. After the reaction mixture was stirred at r.t. overnight, it was diluted with dichloromethane, washed with water, and the product was extracted into dilute aqueous hydrochloric acid solution, which was washed with dichloromethane. The aqueous phase was made alkaline with aqueous sodium hydroxide, and extracted with dichloromethane. The dichloromethane solution was dried over Na2SO4 and evaporated. The product was purified by silicagel chromathography (System E) and recrystallised from absolute ethanol. Yield 0.586 g, 48%. 1H NMR (CDCl3): 7.07 (1H, t, 8.1 Hz), 6.64 (2H, m), 4.01 (2H, q, 7.1 Hz), 3.55 (2H, s), 2.81 (2H, t, 6.1 Hz), 2.67 (2H, t, 6.1 Hz), 2.44 (3H, s), 1.40 (3H, t, 6.8 Hz). 13C NMR (CDCl3): 156.5, 135.9, 126.1, 123.0, 118.4, 108.3, 63.3, 57.9, 52.7, 46.0, 23.8, 14.9; MS (EI+): 191 (83%), 190 (100%), 162 (15%), 160 (16%), 148 (61%), 120 (28%), 104 (48%); Rt (HPLC)=8.1 min.

Workup

  1. washwashed with water
  2. extractionthe product was extracted into dilute aqueous hydrochloric acid solution, which
  3. washwas washed with dichloromethane
  4. extractionextracted with dichloromethane
  5. dry with materialThe dichloromethane solution was dried over Na2SO4
  6. customevaporated
  7. customThe product was purified by silicagel chromathography (System E)
  8. customrecrystallised from absolute ethanol

Sources & evidence

ORD record
ord-0f1604c8a4be4f98aabfe7505b6f90c3
Source dataset
uspto-grants-1999_06
Patent number
US05912342

Reaction notes

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