Tetrahydrofuran → HCID 20196448, compound

HRID 652985Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11](=[O:13])=O.[CH3:14][C:15]([CH3:17])=O.O1[CH2:22][CH2:21][CH2:20][CH2:19]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)P(N(C)C)N(C)C>[CH2:14]([O:13][CH2:11][C:20]([CH2:21][CH2:22][CH2:19][CH2:20][CH2:21][CH2:22][CH2:19][CH2:20][CH2:21][CH2:22][CH2:19][CH2:20][CH2:21][CH2:22][CH2:19][CH2:20][CH2:21][CH3:22])=[CH2:19])[C:15]1[CH:17]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a stirred suspension of 5.0 g of methyl triphenylphosphonium bromide in 50 ml of anhydrous tetrahydrofuran and 4.0 ml of hexamethylphosphorous triamide was gradually added 27 ml of 0.5M potassium bis-trimethylsilylamide. The resultant mixture was then stirred at room temperature for 30 minutes, after which time it was cooled to -60° C. (dry ice/acetone bath) and treated dropwise with a solution of 8.0 g (210 mmol) of the compound of Example 2(b) in 50 ml of anhydrous tetrahydrofuran and stirred for 1 hour at -60° C. and for 1 hour at ice bath temperature. The solids were then filtered off and the filtrate evaporated in vacuo to afford an oil. The oil was then chromatographed on silica gel employing a mixture of petroleum ether and methyl-t-butyl ether in a ratio of 9:1 as the eluent to yield a yellow oil.

Workup

filtrationThe solids were then filtered off
customthe filtrate evaporated in vacuo
customto afford an oil
customThe oil was then chromatographed on silica gel employing
additiona mixture of petroleum ether and methyl-t-butyl ether in a ratio of 9:1 as the eluent
customto yield a yellow oil

Sources & evidence

ORD record: ord-19e97064fd464702a2002870fae2a6b6
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04673672

Reaction notes

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