2-Pentylthiophene → HCID 178442115, compound

HRID 980781Notes

Reaction equation

[CH2:1]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH2:12][CH3:13].B([O-])=O.[Na+]>>[CH2:11]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:8]3[S:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:10][CH:9]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH2:12][CH3:13]

Participants

Reactant 3

HCID 209952-Pentylthiophene

HCID 145326Sodium metaborate

HCID 178447874HCID 178447874, compound

Product 1

HCID 178442115HCID 178442115, compound

Procedure

19 g of 2-[4-(trans-4-n-propylcyclohexyl)-styryl]-5-n-pentylthiophene (obtainable by Friedel Crafts acylation of 2-pentylthiophene with 4-(trans-4-n-propylcyclohexyl)-phenylacetyl chloride and reduction of the resulting ketone with sodium boranate to give the alcohol, followed by dehydration) and 5 g of sulfur are heated to 220° for 3 hours. Subsequent working-up by chromatography gives 8.3 g of 2-[4-trans-4-n-propylcyclohexylphenyl]-5-n-pentylthieno[3,2-b]thiophene.

Sources & evidence

ORD record: ord-7662caccac6240018e35a92eedf953e2
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04639328

Reaction notes

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