Benzoyl chloride → HCID 9844687, compound

HRID 991875Notes

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:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[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:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 9883173HCID 9883173, compound2×

Product 1

HCID 9844687HCID 9844687, 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, 30 mg, 0.097 mmol) and benzoyl chloride (0.041 mL, 0.35 mmol) as described in General Procedure D. [α]D=+97 (EtOAc), PNMR (300 MHz, CDCl3) δ 1.37 (t, 3 H, J=7.1 Hz), 1.66 (m, 3 H), 1.97 (s, 3 H), 2.10(m, 1 H), 2.28 (m,2 H),4.36 (q, 2 H, J=7.1 Hz), 5.78 (d, 1 H, J=16 Hz), 5.92 (s, 1 H), 7.41-7.45 (several ds, 4 H), 7.54 (m, 1 H), 7.95 (dd, 2 H, J=8.4, 1.8 Hz), 8.05 (dd, 2 H, J=8.6, 1.5 Hz). (Trimethylsilyl)ethyl (−)-(E)-4-(4-(6-Hydroxy-2-methylcyclohex-1-enyl)but-3-en-1-ynyl)benzoate (Compound 2a) and (Trimethylsilyl)ethyl (+)-(E)-4-(4-(6-Acetoxy-2-methylcyclohex-1-enyl)but-3-en-1-ynyl)benzoate (Compound 8b).

Sources & evidence

ORD record: ord-0b9636c5fcee42148e4f1dd764e1f94d
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465647B1

Reaction notes

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