Methoxymethyl-triphenylphosphonium chloride → 5-(Methoxymethylene)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 1466021Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].[CH3:12][O:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:35]1[CH2:44][CH2:43][CH2:42][C:41]2[C:40]([C:45]#[N:46])=[CH:39][CH:38]=[CH:37][C:36]1=2.BrC1C=CC=C2C=1CCCC2=O>C1COCC1.O>[CH3:12][O:13][CH:14]=[C:35]1[CH2:44][CH2:43][CH2:42][C:41]2[C:40]([C:45]#[N:46])=[CH:39][CH:38]=[CH:37][C:36]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium bis(trimethylsilyl)amide (2 mL, 4 mmol, 2M in THF) was added to a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (1.47 g, 4.3 mmol) in dry THF (20 mL) at 0° C. for 35 min and a solution of 5-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile [prepared from 5-bromo-tetralone following the procedure described in PCT publication WO2004/071389A2, Intermediate 41](490 mg, 2.86 mmol) in THF (10 mL) added over 10 min. The mixture was stirred at 0° C. for 2 h and at room temperature for 1 h. Water was added and the mixture was partitioned between EtOAc and brine. The organic layer was dried and concentrated. The crude product was purified via preparative-TLC (PE:EtOAc=10:1) to afford the title compound.

Workup

additionadded over 10 min
customthe mixture was partitioned between EtOAc and brine
customThe organic layer was dried
concentrationconcentrated
customThe crude product was purified via preparative-TLC (PE:EtOAc=10:1)

Sources & evidence

ORD record: ord-7387ed66835d488fab7a5a04e3437edb
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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