Isobutyryl chloride → HCID 9951816, compound

HRID 991873Notes

Reaction equation

[OH:1][CH:2]1[C:7](/[CH:8]=[CH:9]/[C:10]#[C:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=[C:6]([CH3:23])[CH2:5][CH2:4][CH2:3]1.[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26]>>[C:24]([O:1][CH:2]1[C:7](/[CH:8]=[CH:9]/[C:10]#[C:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=[C:6]([CH3:23])[CH2:5][CH2:4][CH2:3]1)(=[O:28])[CH:25]([CH3:27])[CH3:26]

Participants

Reactant 2

HCID 62325Isobutyryl chloride

HCID 9883173HCID 9883173, compound2×

Product 1

HCID 9951816HCID 9951816, compound

Procedure

The title compound, a colorless oil, was prepared from ethyl (+)-(E)-4-(4-(6-hydroxy-2-methylcyclohex-1-enyl)but-3-en-1-ynyl)benzoate (Compound 1b, 25 mg, 0.081 mmol) and iso-butyryl chloride (0.084 mL, 0.81 mmol) as described in General Procedure C. [α]D=+138 (EtOAc), PNMR (300 MHz, CDCl3) δ 1.17 (d, 6 H, J=7.7 Hz), 1.39 (t, 3 H, J=7.1 Hz), 1.67 (m, 3 H), 1.92 (s, 3 H), 1.96 (m, 1 H), 2.21 (m, 2 H), 2.54 (m, 1 H, J=7.7 Hz), 4.3 7 (q, 2 H, J=7.1 Hz), 5.66 (s, 1 H), 5.67 (d, 1 H, J=16 Hz), 7.0 8 (d, 1 H, J=16 Hz), 7.48 (d, 2 H, J=8.3 Hz), 7.98 (d, 2 H, J=8.3 Hz).

Sources & evidence

ORD record: ord-c3e87c0aae744efe989547dd0e8fd1e1
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465647B1

Reaction notes

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