Tetrahydrofuran → HCID 10685902, compound

HRID 544412Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[I:19]Cl>>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][I:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 24640Iodine chloride

HCID 10888453Benzene, [(4-pentenyloxy)methyl]-

Product 1

HCID 10685902HCID 10685902, compound

Procedure

5-Benzoxy-1-pentene (30 mmol, 5.7 g) was hydroborated with BH3 -THF (10 mmol) at 0° C. for 1 hr. Iodinemonochloride (20 mmol, 1.0 ml) was added at room temperature; after 45 min,the product was isolated via chromatography (alumina): yield 5.63 g (88% based on ICl); bp 125° C./0.25 torr; m/e 318.1 (Calcd 318.2); IR (neat) 1705(C=O), 1205(C-I)cm-1 ; NMR (neat) δ 1.7 (broad envelope, 6, alkyl), 3.0 (t, 2, --CH2I), 4.2 (t, 2, --CH2O--),7.6 (m, 5, ArH).

Workup

customat 0° C.
customfor 1 hr
customthe product was isolated via chromatography (alumina)

Sources & evidence

ORD record: ord-646a7cf5a6c84f4787192712fa0b4e96
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04450149

Reaction notes

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