2-Methoxybenzaldehyde → HCID 66930885, compound

HRID 511957Notes

Reaction equation

HRID 511957 reaction equation
[Br-].[O:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:44][O:45][C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[CH:48]=O>C1COCC1>[CH3:44][O:45][C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[CH:48]=[CH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 3251421Potassium bis(trimethylsilyl)amideHCID 71515132HCID 71515132, compound

Product 1

HCID 66930885HCID 66930885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Methoxyphenyl)-7-phenoxy-1-heptene (7.3) was synthesized as described in 7.1 using 6.1 (2.0 g, 3.85 mmol), dry THF (30 mL), potassium bis(trimethylsilyl)amide (0.77 g, 3.85 mmol), and 2-methoxybenzaldehyde (0.20 g, 1.47 mmol). The title compound (7.3) was isolated as a colorless liquid after purification by flash column chromatography (0.396 g, 91% yield, predominantly cis, cis:trans=93:7).

Workup

  1. custom1-(2-Methoxyphenyl)-7-phenoxy-1-heptene (7.3) was synthesized

Sources & evidence

ORD record
ord-ab2dd50e9eb74723806c0aacb2fc0c65
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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