(S)-1,2-Decanediol → 2-n-Octyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine

Reaction equation

[CH3:1][O:2][C:3]1[C:7]([O:8][CH3:9])=[CH:6][S:5][CH:4]=1.[CH2:10](O)[C@@H:11](O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]CC>>[CH2:10]([CH:1]1[O:2][C:3]2=[CH:4][S:5][CH:6]=[C:7]2[O:8][CH2:9]1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 2733662(S)-1,2-Decanediol

HCID 36135013,4-Dimethoxythiophene

Product 1

HCID 99213252-n-Octyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine

Procedure

Chiral 2-n-octyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine was synthesized by transetherification of 3,4-dimethoxythiophene with (S)-1,2-decanediol and purified to a purity of 99.24% as described in INVENTION EXAMPLE 1. It was characterized by GC-MS and 1H-NMR-spectroscopy, and exhibited a specific rotation of −88° at 25° C. and 436 nm in hexane.

Workup

custompurified to a purity of 99.24%
customa specific rotation of −88°
customat 25° C.

Sources & evidence

ORD record: ord-0c7091e2d6c4451cab60f2773711d577
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094865B2

Reaction notes

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