Cyclopropanecarboxaldehyde → HCID 90253544, compound

HRID 1478718Notes

Reaction equation

C1(C=O)CC1.C[C@H]([C@@:10]1([OH:20])[CH2:15][C@@H:14](C)[CH2:13][CH2:12][C@@H:11]1[CH:17]([CH3:19])C)C=C.CC1C[C@H](O)[C@@H](C(C)C)CC1>>[CH:11]1([C@H:10]([OH:20])[CH2:15]/[CH:14]=[CH:13]/[CH3:12])[CH2:17][CH2:19]1

Participants

Reactant 3

HCID 123114Cyclopropanecarboxaldehyde

HCID 12285346HCID 12285346, compound

HCID 42604962HCID 42604962, compound

Product 1

HCID 90253544HCID 90253544, compound

Procedure

Using the method described by J. Nokami et al., J. Am. Chem. Soc. 2001, 123, 9168-9169, cyclopropanecarbaldehyde was reacted with (1S,2R,5S)-1-[(2S)-but-3-en-2-yl]-5-methyl-2-(propan-2-yl)cyclohexanol [this crotylation reagent was derived from (+)-menthol] to afford the product as an oil. Yield: 600 mg, 4.75 mmol, 100%. 1H NMR (400 MHz, CDCl3), characteristic peaks: δ 5.45-5.63 (m, 2H), 2.86-2.92 (m, 1H), 2.33-2.41 (m, 1H), 2.20-2.29 (m, 1H), 1.69-1.72 (m, 3H), 0.47-0.56 (m, 2H), 0.27-0.37 (m, 1H), 0.16-0.26 (m, 1H).

Sources & evidence

ORD record: ord-23df10c1cd564176a3ed03cfaed6b0ec
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403846B2

Reaction notes

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