Ammonium Chloride → HCID 131719623, 화합물

HRID 481991노트

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HRID 481991 반응식
Cl[C@H:2]([Br:21])[CH2:3][CH2:4][CH2:5][CH2:6][B:7]([O:9][C:10]12[CH2:18][CH:14]([C:15]1([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11]2([OH:20])[CH3:19])[OH:8].[CH3:22][Mg].[Cl-].[NH4+]>C1COCC1>[C:10]12([OH:9])[CH2:18][CH:14]([C:15]1([CH3:17])[CH3:16])[CH2:13][CH2:12][C:11]2([OH:20])[CH3:19].[Br:21][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([B:7]([O-:8])[O-:9])[CH3:22]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 131719624HCID 131719624, 화합물HCID 178477778HCID 178477778, 화합물

생성물 1

HCID 131719623HCID 131719623, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

In a 500 ml round bottomed flask, 300 ml of anhydrous THF and the crude pinanediol (R)-1-chloro-5-bromopentylboronate from the previous reaction (assuming 89 g; 0.247 moles) were mixed and cooled to -78° C. with stirring under argon. To the solution was added methylmagnesium bromnide (3.26N, 79.6 ml). The solution was warmed to room temperature overnight. Petroleum ether (500 ml) and saturated ammonium chloride (250 ml) were added, forming an emulsion. The aqueous phases were separated. The organic phase was washed with saturated ammonium chloride (2×250 ml), causing the emulsion to disappear. The combined aqueous phases were washed with petroleum ether (2×250 ml). The combined organic phases were dried over sodium sulfate, filtered and evaporated under vacuum to yield 85.85 g of crude pinanediol (R)-5-bromo-1-methylpentylboronate.

후처리

  1. additionwere mixed
  2. temperatureThe solution was warmed to room temperature overnight
  3. customforming an emulsion
  4. customThe aqueous phases were separated
  5. washThe organic phase was washed with saturated ammonium chloride (2×250 ml)
  6. washThe combined aqueous phases were washed with petroleum ether (2×250 ml)
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-2d0550abe54343ca8e315b63e24a2ec3
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05792772

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