Tetrahydrofuran → HCID 70272151, compound

HRID 1004466Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8](C=O)=[CH:7][CH:6]=1)[CH2:2][CH3:3].[Br-].[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:16])=[O:15].[CH2:41]1COCC1>>[CH2:1]([O:4][C:5]1([CH:41]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][CH:8]=[CH:11][CH2:12]1)[CH2:2][CH3:3]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 798124-Propoxybenzaldehyde

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

Product 1

HCID 70272151HCID 70272151, compoundYield 60%

Procedure

This compound was synthesized from p-propoxybenzaldehyde (3.26 g, 20 mmol, prepared from 1-bromopropane and 4-hydroxybenzaldehyde) and 5-carboxypentyltriphenylphosphonium bromide (9.50 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (petroleum ether) afforded the product (3.15 g, 60%) as white crystals (mp: 52-53° C.). IR: 3450-2500, 1730 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.48 (m, 2H), 1.67 (m, 2H), 1.82 (m, 2H), 2.35 (m, 4H), 3.92 (t, 2H), 5.72+6.05 (m, 1H), 6.35 (d, 1H), 7.05 (q, 4H), 10.40 (bs, 1H). Anal. Calcd. for C16H22O3 : C, 73.25, H, 8.45%. Found: C, 73.15, H, 8.45%. Z:E=30:70.

Workup

customCrystallization (petroleum ether)

Sources & evidence

ORD record: ord-48b353ce6c584e218e0e17dadb543724
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06048989

Reaction notes

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