1-(Hex-5-ynyl)-4-phenyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane → 1-(Hex-5ynyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane

HRID 129285Notes

Reaction equation

HRID 129285 reaction equation
[CH2:1]([C:5]12[CH2:12][S:11][C:8]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18])([S:9][CH2:10]1)[O:7][CH2:6]2)[CH2:2][CH2:3]C.C(C12CSC(CCCCC#C)(SC1)OC2)(C)(C)C.C(C12CSC(CCCCC#C)(SC1)OC2)C(C)C.C(C12SCC(C3C=CC=CC=3)(CS1)CO2)CCCC#C.C1(CC23CSC(CCCCC#C)(SC2)OC3)CC1.C(C(CO)(CS)CS)CCC.C(C(CO)(CS)CS)(C)(C)C.C(C(CO)(CS)CS)C(C)C.OC(C1C=CC=CC=1)(CS)C(C)S.C1(CC(CO)(CS)CS)CC1>>[CH2:13]([C:8]12[S:9][CH2:10][C:5]([CH2:1][CH2:2][CH3:3])([CH2:12][S:11]1)[CH2:6][O:7]2)[CH2:14][CH2:15][CH2:16][C:17]#[CH:18]

Participants

11

Reactant 10

HCID 193732651-(Hex-5-ynyl)-4-phenyl-2-oxa-6,7-dithiabicyclo[2.2.2]octaneHCID 193732674-i-Butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octaneHCID 193732792-n-Butyl-2-hydroxymethylpropan-1,3-dithiolHCID 193733084-t-Butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octaneHCID 193733134-n-Butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octaneHCID 193733312-Hydroxy-methyl-2-phenylpropan-1,3-dithiolHCID 193733982-t-Butyl-2-hydroxymethylpropan-1,3-dithiolHCID 193734024-Cyclopropylmethyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octaneHCID 231725902-i-Butyl-2-hydroxymethylpropan-1,3-dithiolHCID 537500442-Cyclopropylmethyl-2-hydroxymethylpropan-1,3-dithiol

Product 1

HCID 193733381-(Hex-5ynyl)-4-n-propyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane

Procedure

In an analogous manner 4-n-butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octane, 4-t-butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octane, 4-i-butyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octane, 1-(hex-5-ynyl)-4-phenyl-2-oxa-6,7-dithiabicyclo[2.2.2]octane and 4-cyclopropylmethyl-1-(hex-5-ynyl)-2-oxa-6,7-dithiabicyclo[2.2.2]octane were prepared from trimethyl orthohept-6-ynoate and 2-n-butyl-2-hydroxymethylpropan-1,3-dithiol, 2-t-butyl-2-hydroxymethylpropan-1,3-dithiol, 2-i-butyl-2-hydroxymethylpropan-1,3-dithiol, 2-hydroxy-methyl-2-phenylpropan-1,3-dithiol and 2-cyclopropylmethyl-2-hydroxymethylpropan-1,3-dithiol respectively.

Sources & evidence

ORD record
ord-2709eb2110a746aeae8a62332b09c528
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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