2-Butyn-1-ol → HCID 16739236, compound

HRID 430034Notes

Reaction equation

HRID 430034 reaction equation
[Cl-].[Ca+2].[Cl-].[CH2:4](Br)[C:5]1[CH:13]=[CH:12][C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=1.[CH2:15]([OH:19])[C:16]#[C:17][CH3:18]>[O-2].[Zn+2].ClC(Cl)C>[CH2:15]([O:19][CH2:4][C:5]1[CH:13]=[CH:12][C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=1)[C:16]#[C:17][CH3:18]

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 5284359Calcium ChlorideHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-

Product 1

HCID 16739236HCID 16739236, compound

Reagents, catalysts & solvents 2

HCID 3007857Zinc OxideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a flask equipped with magnetic stirred condenser and drying tube filled with calcium chloride, 3.0 g, (13.95 mmol) of piperonyl bromide, 2.0 g (27.9 mmol) of 2-butyn-1-ol and 50 ml of dichloroethane are placed. After the addition of zinc(II) oxide (1.1 g, 13.5 mmol) the suspension is stirred at room temperature for 1 hour. The reaction is accompanied by a characteristic chance of colour. The mixture is then filtered, the filtrate is evaporated. The residual oil is dissolved in 50 ml of ether, washed within 2×10 ml of water, dried and evaporated. Yield 2.3 g (11.2 mmol, 80.7%), GC 82%. IR(CHCl3, cm−1) υ: 2997, 2946, 2921, 2888, 2376, 1609, 1503, 1491, 1445, 1251, 1099, 1070, 1042, 937, 865, 810; 1H-NMR (400 MHz, CDCl3) δ: 1.87 (3H, t, J=2.3 Hz, Me), 4.10 (2H, q, J=2.3 Hz, O—CH2—C≡), 4.47, (2H, s, O—CH2—Ar), 5.94 (2H, s, O—CH2—O), 6.76 (1H, d, J=8 Hz, H-7), 6.81 (1H, dd, J=8.15 Hz, H-6), 6.86 (1H, J=1.5 Hz, H-4); 13C-NMR (100 MHz, CDCl3) δ: 3.52 (Me), 57.29 (O—CH2—C≡), 71.15 (O—CH2—Ar), 82.54 (CH3—C≡), 100.9 C-2, 107.95, 108.71 (C-4, 7), 121.66 (C-6), 131.39, (C-5), 147.15, 147.66 (C3a, C-7a);

Workup

  1. customTo a flask equipped with magnetic stirred condenser
  2. customdrying tube
  3. filtrationThe mixture is then filtered
  4. customthe filtrate is evaporated
  5. dissolutionThe residual oil is dissolved in 50 ml of ether
  6. washwashed within 2×10 ml of water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-c6b603ecff3145b79f88869419304ae6
Source dataset
uspto-grants-2001_11
Patent number
US06320085B1

Reaction notes

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